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

HRID 127107노트

반응식

HRID 127107 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3286c0833c484dd2b65382c1b2746537
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254260

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