939-69-5, 6-Hydroxybenzo[d]thiazole-2-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
939-69-5, b. Synthesis of 2-cyano-6-hydroxybenzothiazole dimethyl phosphate ester. Five hundred mg (2.84 mmoles) of 2-cyano-6-hydroxybenzothiazole was placed in a 10 mL reactor vial, which could be sealed with a teflon cap and had a magnetic stir bar. A 5.0 mL aliquot of THF was added and upon stirring the 2-CBT dissolved rapidly giving a clear, light red solution. This was followed by the addition of 0.550 mL (402 mg. 3.97 mmoles) of triethylamine. The resulting clear solution was cooled to 4° C. by placing it in an ice bath. Next, 512 mg (3.54 mmoles) of dimethylchlorophosphate dissolved in 1.5 mL of THF was added to this solution over a period of 60 seconds. After approximately 20 minutes, the 10 mL reactor vial was removed from the ice bath and allowed to stir for two hours at room temperature. At this point the reaction was a thick slurry. The triethylammonium chloride salt was removed by suction filtration. The filtrate was transferred to a round-bottomed flask and concentrated on a rotoevaporator under vacuum. The residue was dissolved in 50 mL of ethyl acetate followed by the addition of 20 mL of water plus 10 mL of water saturated with NaCl. The phases were separated and the ethyl acetate layer was saved. The aqueous phase was back washed with 40 mL of ethyl acetate and this was combined with the previous ethyl acetate layer. The combined ethyl acetate solution was washed twice with a mixture of 15 mL of aqueous saturated NaCl and 5 mL of water. The ethyl acetate layer was dried over MgSO4, filtered and concentrated on a roto-evaporator at full vacuum. Approximately 5 mL of ethyl ether was added to the concentrate which dissolved the thick oil. This was cooled to -20° C. and white crystals formed rapidly. The white crystals were isolated by filtration. The melting point of the product, 2-cyano-6-hydroxybenzothiazole dimethylphosphate ester, (6-CBT-DMP) was 54.0°-55.1° C. The HPLC showed a purity of 96.4percent (by area). The column was 3.9 mm*25 mm with a flow rate of 1.0 mL/min with a linear program from 100percent water to 100percent methanol with a program time of 30 minutes. The product was monitored at 254 nm. The retention time for the product was 23.4 minutes. The NMR spectrum was determined. The solvent used for the NMR was deuterochloroform with TMS as an internal standard. There was a doublet centered at delta 3.9 with a coupling constant of 10 Hz and integrated for 6.00H’s. There was a multiplet centered at 7.9 which integrated for 3.08 hours.
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Reference：
Patent; JBL Scientific, Inc.; US5424440; (1995); A;,
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