Hydrochloric Acid → 2-Sulfamoyl-1,3-benzothiazol-5-yl cyclopentylacetate

HRID 2295753Notes

Reaction equation

HRID 2295753 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.[CH:22]1([CH2:27][C:28](Cl)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23]1.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH:22]1([CH2:27][C:28]([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:29])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12159529927-14-8HCID 3485182Cyclopentylacetyl chloride

Product 1

HCID 540433662-Sulfamoyl-1,3-benzothiazol-5-yl cyclopentylacetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 5-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 cyclopentaneacetyl chloride (1.6 g., 0.01 mole). The reaction mixture is stirred at 25° C. for 2 hours, poured into ice water and excess hydrochloric acid and extracted into ether. The organic extract is washed with water and dried over magnesium sulfate. The ether is evaporated and the residue chromatographed on silica gel (130 g. 70-230 mesh) to give 2-sulfamoyl-5-benzothiazolyl cyclopentaneacetate.

Workup

  1. extractionextracted into ether
  2. extractionThe organic extract
  3. washis washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe ether is evaporated
  6. customthe residue chromatographed on silica gel (130 g. 70-230 mesh)

Sources & evidence

ORD record
ord-6eba10271a8846f2bbb687b9d5471ed6
Source dataset
uspto-grants-1984_01
Patent number
US04426388

Reaction notes

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