Thioglycolic Acid → 4,5-Diphenyl-2-oxazolyl mercaptoacetic acid

HRID 1580806

反応式

HRID 1580806 の反応式
[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].C[O-].[Na+].Cl[C:10]1[O:11][C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1>C1COCC1>[C:15]1([C:13]2[N:14]=[C:10]([CH:2]([SH:3])[C:1]([OH:5])=[O:4])[O:11][C:12]=2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 1133Thioglycolic AcidHCID 10942334Sodium MethoxideHCID 131311622-Chloro-4,5-diphenyloxazole

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

8.15 g. of the cyclohexyl ester of thioglycolic acid is dissolved in 80 ml. of absolute THF, and 2.6 g. of sodium methylate is added thereto. The reaction mixture is agitated for 15 minutes. Then, 12 g. of 2-chloro-4,5-diphenyl-oxazole (b.p. 170°/0.05 mm.; producible by reacting 4,5-diphenyl-2-oxazolone with POCl3) in 20 ml. of THF is added dropwise. The reaction mixture is refluxed under agitation for 9 hours. The thus-precipitated NaCl is filtered off and the filtrate concentrated by evaporation, thus obtaining the cyclohexyl ester of 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid as an oily residue. The latter 16 g.) is refluxed in 150 ml. of ethanol with 8 g. of pulverized K2CO3 for 2 hours. After conducting the usual working-up operation, 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid is obtained, m.p. 137°-138°.

後処理

  1. temperatureThe reaction mixture is refluxed under agitation for 9 hours
  2. filtrationThe thus-precipitated NaCl is filtered off
  3. concentrationthe filtrate concentrated by evaporation

出典と根拠

ORDレコード
ord-a3af9fe1d3454831988a96387a96a0e4
出典データセット
uspto-grants-1976_01
特許番号
US03933840

関連ノート

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