N,N-二甲基甲酰胺 → 4,5-Diphenyl-2-oxazolyl mercaptoacetic acid

HRID 2072545

反应方程式

HRID 2072545 反应方程式
[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

参与物

4

反应物 3

HCID 6228N,N-二甲基甲酰胺HCID 953432-氯-2-苯基苯乙酮HCID 23423126(Carbamoylsulfanyl)acetic acid

产物 1

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

实验过程

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°.

后处理

  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

来源与证据

ORD记录
ord-156f575e82c1420193bc723d5471a5db
来源数据集
uspto-grants-1977_09
专利号
US04051250

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