Benzenesulfonyl chloride → ethyl {2-[(phenylsulfonyl)amino]-1,3-thiazol-4-yl}acetate

HRID 127107Notes

Reaction equation

HRID 127107 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:13]1([S:19]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl ester

Product 1

HCID 717505ethyl {2-[(phenylsulfonyl)amino]-1,3-thiazol-4-yl}acetateYield 58.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 2-aminothiazol-4-ylacetate (18.6 g.) in pyridine (140 ml.) was added benzenesulfonyl chloride (17.7 g.), and the mixture was stirred for 50 minutes at 90° to 100° C., and then pyridine was distilled off under reduced pressure. To the residue was added 10% hydrochloric acid (200 ml.), and then extracted with ethyl acetate (100 ml.). The extract was washed with a saturated sodium chloride aqueous solution (50 ml.×2) and treated with an activated carbon and then dried. After distillation of ethyl acetate from the extract, the precipitated crystals were collected by filtration and washed with diethyl ether and dried to give ethyl 2-benzenesulfonamidothiazol-4-ylacetate (19.0 g.), mp 129° to 130° C.

Workup

  1. distillationpyridine was distilled off under reduced pressure
  2. additionTo the residue was added 10% hydrochloric acid (200 ml.)
  3. extractionextracted with ethyl acetate (100 ml.)
  4. washThe extract was washed with a saturated sodium chloride aqueous solution (50 ml.×2)
  5. additiontreated with an activated carbon
  6. customdried
  7. distillationAfter distillation of ethyl acetate from the extract
  8. filtrationthe precipitated crystals were collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-3286c0833c484dd2b65382c1b2746537
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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