Dimethylformamide → 4,5-Diphenyl-2-oxazolyl mercaptoacetic acid

HRID 2072545

반응식

HRID 2072545 반응식
[C:1]1([C:7](=[O:16])[CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([S:20][CH2:21][C:22]([OH:24])=[O:23])(=O)N.[CH3:25][N:26](C=O)C>>[C:10]1([C:8]2[N:26]=[C:25]([CH:21]([SH:20])[C:22]([OH:24])=[O:23])[O:16][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 95343Ethanone, 2-chloro-1,2-diphenyl-HCID 23423126(Carbamoylsulfanyl)acetic acid

생성물 1

HCID 214083604,5-Diphenyl-2-oxazolyl mercaptoacetic acid

실험 절차

23 g. of 1,2-diphenyl-2-chloroethanone is heated together with 18 g. of the ethyl ester of carbamoylmercaptoacetic acid in 150 ml. of absolute DMF for 3 hours to 70°. Then, the DMF is removed, and the residue, containing the ethyl ester of N-(1,2-diphenyl-2-oxoethyl)-carbamoylmercaptoacetic acid, is refluxed for 5 hours with a mixture of 100 g. of POCl3 and 200 ml. of benzene. The mixture is then evaporated under reduced pressure and the residue is purified by chromatography on silica gel, thus obtaining the ethyl ester of 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid, m.p. 54°-56°.

후처리

  1. customThen, the DMF is removed
  2. additionthe residue, containing the ethyl ester of N-(1,2-diphenyl-2-oxoethyl)-carbamoylmercaptoacetic acid
  3. temperatureis refluxed for 5 hours with a mixture of 100 g
  4. customThe mixture is then evaporated under reduced pressure
  5. customthe residue is purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-156f575e82c1420193bc723d5471a5db
출처 데이터셋
uspto-grants-1977_09
특허 번호
US04051250

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