Hydrochloric Acid → HCID 54503996, compound

HRID 2295752Notes

Reaction equation

HRID 2295752 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[N:7][C:6]=2[CH:14]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](Cl)=[O:31])=[CH:25][CH:24]=1.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:1][C:2]2[CH:3]=[CH:4][C:5]3[S:9][C:8]([S:10](=[O:12])(=[O:11])[NH2:13])=[N:7][C:6]=3[CH:14]=2)=[O:31])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 906924-Chlorophenylacetyl chlorideHCID 12159529927-14-8

Product 1

HCID 54503996HCID 54503996, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-hydroxy-2-benzothiazolesulfonamide 1.15 g., 0.005 mole) triethylamine (0.7 ml, 0.005 mole) and 4-dimethylaminopyridine (5 mg, catalyst) in dimethylformamide (10 ml) is added 2-(4-chlorophenyl)acetyl chloride (0.8 ml). The reaction mixture is stirred for 2 hours, poured into ice water, acidified with hydrochloric acid and extracted with ether. The organic extract is washed with water and dried over magnesium sulfate. The ether is distilled at reduced pressure and the residue chromatographed on silica gel as eluant (130 g, 70-230 mesh) using ethylacetatehexane (1:1) to give 2-sulfamoyl-5-benzothiazolyl 2-(4-chlorophenyl)acetate.

Workup

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. washis washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe ether is distilled at reduced pressure
  6. customthe residue chromatographed on silica gel as eluant (130 g, 70-230 mesh)

Sources & evidence

ORD record
ord-f56c0562b2cb4d50aff528e689e7d11a
Source dataset
uspto-grants-1984_01
Patent number
US04426388

Reaction notes

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