Synthesis of some 4-alkoxy- and 6-alkoxy-2-benzo-thiazolylamides was written by Mndzhoyan, A. L.;Azaryan, A. S.;Iradyan, M. A.;Aroyan, A. A.. And the article was included in Azerbaidzhanskii Khimicheskii Zhurnal in 1967.Name: 6-Butoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:
o- and p-Alkoxynitrobenzenes are hydrogenated over Ni-Cr2O3 to give o- and p-alkoxyanilines (I). Treating I with KSCN and Br gave the corresponding II and III, resp., which were converted into the corresponding amides (IV) and (V), resp. Thus, a mixture of 0.3 mole alkoxynitrobenzene, 50 cc. EtOH, and 4 g. Ni-Cr2O3 catalyst was hydrogenated in an autoclave at 110-20°/100 atm. for 10-12 hrs., filtered, and distilled to give 74.8-86.3% I. From I the following II and III were prepared (R, m.p., m.p. hydrochloride, and % yield given): 6-Et, 159-60°, 199-200°, 60.9; 4-Et, 76-8°, 176-8°, 51.9; 6-Pr, 127-9°, 189-90°, 86.5; 6-iso-Pr, 158-9°, 191-3°, 80.2; 4-Pr, 114-15°, 160-1°, 51.2; 6-Bu, 119-21°, 140-1°, 89.6; 6-iso-Bu, 160-1°, 189-91°, 69.1. A mixture of 0.05 mole acyl chloride and 150 cc. 1:1 Me2CO-dioxane placed in a flask connected with extractor in which a paper extraction shell containing 0.1 mole II or III was placed, was heated on a water bath to complete solution of II or III, filtered, washed with Me2CO, and crystallized from EtOH to obtain the following IV (R, R1, m.p., and % yield given): Et, iso-PrCO, 91-2°, 45.5; Et, Bz, 109-10°, 80.5; Et, MeOC6H4CO (A), 120-2°, 85.3; Et, EtOC6H4CO (B), 116-18°, 76; Et, PrOC6H4CO (C), 94-7°, 84.1; Et, iso-PrOC6H4CO (D), 94-6°, 84.2; Et, BuOC6H4CO (E), 97-8°, 81; Et, PhSO2 (F), 155-7°, 87.4; Et, 2-furoyl (G), 129-30°, 83.3; Et, 2-benzofuroyl (H), 152-4°, 71.8; Et, 2-(2,3-dihydrobenzofuroyl) (I), 110-12°, 70.6; Pr, EtC6H4CO, 191-2°, 79; Pr, G, 224-5°, 80.9; Pr, I, 169-70°, 79.1; and the following V (same data): Et, PrCO, 172-3°, 53.3; Et, iso-PrCO, 140-1°, 45.4; Et, Bz, 222-5°, 87.2; Et, A, 198-200°, 86.9; Et, B, 212-13°, 70.1; Et, C, 224-6°, 84.7; Et, D, 197-200°, 73; Et, F, 199-202°, 60.1; Et, E, 202-3°, 68; Et, iso-BuOC6H4CO, 221-2°, 60; Et, G, 158-9°, 51.9; Et, H, 216-17°, 64.6; Et, I, 142-3°, 90.5; Pr, Bz, 220-2°, 69.2; Pr, A, 145-6°, 80; Pr, B, 204-6°, 86.8; Pr, C, 192-4°, 81.1; Pr, D, 189-90°, 91.8; Pr, E, 197-8°, 67.9; Pr, F, 200-2°, 85.4; Pr, G, 151-2°, 79.5; Pr, H, 212-13°, 65.3; Pr, I, 120-1°, 73.4; iso-Pr, iso-PrCO, 136-9°, 40.3; iso-Pr, BuCO, 138-40°, 49; iso-Pr, Bz, 225-6°, 83.7; iso-Pr, A, 228-9°, 73.1; iso-Pr, B, 215-16°, 60; iso-Pr, F, 255-6°, 68.8; iso-Pr, G, 181-4°, 58.6; Bu, BuCO, 140-1°, 70.6; Bu, Bz, 184-6°, 84.6; Bu, A, 181-2°, 50.1; Bu, B, 182-4°, 81.1; Bu, E, 195-7°, 69.8; Bu, H, 158-60°, 76.5; iso-Bu, A, 222-3°, 85.1; Et, ClCH2CO, 170-1°, 81.4; Bu, ClCH2CO, 172-3°, 70.4. A mixture of 0.03 mole Et2NH, 25 cc. EtOH, 0.01 mole (N-6-alkoxy-2-benzothiazolyl)-2-chloroacetamide, and 25 cc. EtOH was heated on a water bath 2-3 hrs., EtOH was distilled, the residue alkalized with 10% NaHCO3 and extracted with Et2O, the extract dried with Na2SO4 and distilled to give the corresponding V: (R, R1, b.p./mm., m.p., and % yield given): Et, Et2NCH2CO, 218-20°/5, 90-2°, 31.9; Bu, Et2NCH2CO, 130-3°/5, 121-2°, 48.3. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Name: 6-Butoxybenzo[d]thiazol-2-amine).
6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Name: 6-Butoxybenzo[d]thiazol-2-amine
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica