King, L. Carroll; Hlavacek, Robert J. published an article in 1950, the title of the article was Reaction of ketones with iodine and thiourea.Formula: C9H7IN2S And the article contains the following content:
cf. C.A. 42, 6360f. The ketone (0.1 mol.), 0.2 mol. CS(NH2)2, and 0.1 mol. iodine, heated overnight on the steam bath, give the substituted 2-aminothiazole; the cooled reaction product is extracted with ether, the residue in boiling H2O filtered, the filtrate made alk. with concentrated NH4OH, and the precipitate crystallized from aqueous EtOH; if the product is an oil, it is crystallized from Skellysolve C. The m.ps. of the Ac derivatives are given in parentheses. 4-Substituted 2-aminothiazoles: p-chlorophenyl, m. 163-4°, 89% [254-5°]; p-bromophenyl, m. 180-1°, 93% [277-8°]; p-iodophenyl, m. 176-7°, 97% [302-3°]; p-methoxyphenyl, m. 204-5°, 72% [287-8°]; p-(methylmercapto)phenyl, m. 180-2°, 67% [232-3°]; p-aminophenyl, m. 174-5°, 63% [di-Ac derivative, m. 284-6°]; p-biphenylyl, m. 207-8°, 99% [252-3°]; p-tolyl, m. 124-5°, 84% [204-5°]; m-isomer, m. 79-92°, 64% [211-12°]; o-isomer, m. 81-2°, 70% [143-4°]; p-nitrophenyl, m. 285-6°, 99% [306-7°]; m-isomer, m. 188-90°, 84% [312-14°]; 2-naphthyl, m. 153-4°, 99% [239-40°]; 2-phenanthryl, m. 243-4°, 87% [304-5°]; 2-thienyl, m. 127-30°, 91% [199-207°]; tert-Bu, m. 98-9°, 71% [173-4°]; ο-hydroxyphenyl, m. 139-40°, 37% [di-Ac derivative, m. 200-3°; HI salt, m. 220-3° (each HI salt has 1 mol. H2O)]; m-isomer, m. 136-8°, 59% [di-Ac derivative, 186-7°; HI salt, 95-7°]; p-isomer, m. 198-200°, 62% [di-Ac derivative, m. 235-7°; HI salt m. 240-2°]; 4-phenyl-5-Et, m. 68-9°, 65% [175-6°]; 4-phenyl-5-Bu, m. 103-4°, 54% [135-6°]; 4-phenyl-5-Bu, m. 60-1°, 43% [187-8°]; 4-benzyl-5-Ph, m. 139-40°, 83% [164-5°]; 4,5-di-Ph, m. 184-5°, 99% [208-9°]; 4-phenyl-5-benzoyl, m. 215-16°, 18% [237-8°]. The aminothiazole from 4-methylcyclohexanone, C8H12N2S, m. 98-9°, 66% [162-3°]; the 3-isomer gives 24% 2-amino-5(or -7)-methyl-4,5,6,7 -tetrahydrobenzothiazole, m. 110-11° [150-1°]. Compound from cycloheptanone, C8H12N2S, m. 75-6° 60% [124-5°]; from hydrindone, C10H8N2S, m. 213-14°, 53% [284-5°]; from 3,4-dihydro-1(2H)-naphthalenone, m. 133-4°, 52% [233-4°]; acenaphthenone gives 99% 8-aminoacenaphtho-1,2-thiazole, bright red, m. 205-7° [309-11°]. Bromoacetomesitylene (4.6 g.) yields 3.8 g. 2,4,6-trimethylphenacylisothiuronium bromide, m. 280-2°; it could not be cyclized to a thiazole. The experimental process involved the reaction of 2-Amino-4-(4-iodophenyl)thiazole(cas: 31699-14-6).Formula: C9H7IN2S
2-Amino-4-(4-iodophenyl)thiazole(cas:31699-14-6) belongs to thiazole. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Formula: C9H7IN2S
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica