Hydrochloric Acid → HCID 54518810, compound

HRID 1649383Notes

Reaction equation

HRID 1649383 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.C(N(CC)CC)C.[C:22](Cl)(=[O:31])[CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:25]1([CH:24]=[CH:23][C:22]([O:1][C:2]2[CH:14]=[CH:13][C:5]3[N:6]=[C:7]([S:9](=[O:11])(=[O:10])[NH2:12])[S:8][C:4]=3[CH:3]=2)=[O:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 54518810HCID 54518810, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (2.3 g., 0.01 mole), 4-dimethylaminopyridine (100 mg., catalyst) and triethylamine (1.4 ml., 0.01 mole) in dimethylformamide (20 ml.) is added cinnamoyl chloride (1.7 g., 0.01 mole). The reaction mixture is stirred at 25° C. for 2 hours and then poured into ice water and excess hydrochloric acid to give 3.5 g. of 2-sulfamoyl-6-benzothiazolyl 3-phenyl-2-propenoate which melts at 235°-235° C. after recrystallization from ethyl acetatehexane.

Workup

  1. customto give 3.5 g
  2. customof 2-sulfamoyl-6-benzothiazolyl 3-phenyl-2-propenoate which melts at 235°-235° C. after recrystallization from ethyl acetatehexane

Sources & evidence

ORD record
ord-713df523bb884ec69a8ebaa0fb2ef7e9
Source dataset
uspto-grants-1983_11
Patent number
US04416890

Reaction notes

Loading…