Hydrochloric Acid → Diethyl 2-sulfamoyl-1,3-benzothiazol-6-yl phosphate

HRID 1263215Notes

Reaction equation

[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9]([NH2:12])(=[O:11])=[O:10])[S:8][C:4]=2[CH:3]=1.[CH3:15][CH2:16][O:17][P:18](Cl)([O:20][CH2:21][CH3:22])=[O:19].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:15][CH2:16][O:17][P:18]([O:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9]([NH2:12])(=[O:11])=[O:10])[S:8][C:4]=2[CH:3]=1)([O:20][CH2:21][CH3:22])=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (2.3 g, 0.01 mole) and 4-dimethylaminopyridine (200 mg) in pyridine (20 ml) was added chlorodiethylphosphate (1.45 ml, 0.01 mole). After stirring for 4 hours at 25° C. additional chlorodiethylphosphate (1.5 ml) was added and the reaction mixture was stirred at 25° C. for 18 hours then poured into ice water and excess hydrochloric acid to give 1.15 g of diethyl(2-sulfamoyl-6-benzothiazolyl)phosphate m.p. 142°-144° C. after recrystallization from ethylene chloride.

Workup

additionwas added

Sources & evidence

ORD record: ord-cd78816f0fae4ad7b32e21a0e00b579c
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04456599

Reaction notes

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