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

HRID 127107ノート

反応式

HRID 127107 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3286c0833c484dd2b65382c1b2746537
出典データセット
uspto-grants-1981_03
特許番号
US04254260

反応ノート

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