Thioglycolic Acid → 2-(2,5-Dichlorophenyl)-2-mercaptoacetic acid

HRID 248598

反応式

HRID 248598 の反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[Cl:9].[OH-].[K+].[C:12]([OH:16])(=[O:15])[CH2:13][SH:14].ClSC(Cl)(C1C=CC=CC=1)C([O-])=O.ClC1C(Cl)=C(S)C=CC=1>CN1CCCC1=O>[Cl:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[CH:13]([SH:14])[C:12]([OH:16])=[O:15]

参加物

7

反応物 5

HCID 1133Thioglycolic AcidHCID 14797Potassium HydroxideHCID 150332-Bromo-1,4-dichlorobenzeneHCID 1402022,3-DichlorobenzenethiolHCID 86746840HCID 86746840、化合物

生成物 1

HCID 224923292-(2,5-Dichlorophenyl)-2-mercaptoacetic acid収率 60.5%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To a 500 ml flask equipped with a thermometer, a condenser and a stirrer were added 45.2 g (0.2 mol) of 1-bromo-2,5-dichlorobenzene, 23.7 g (0.4 mol) of 95% potassium hydroxide, 18.4 g (0.2 mol) of thioglycolic acid and 320 g of N-methyl-2-pyrrolidone, followed by stirring at 140° to 150° C. for 2 hours. Assay of the reaction solution by high performance liquid chromatography identified the solution as a mixture of dichlorophenylthioglycolate and dichlorothiophenol salt. Then, after distilling off the solvent, 300 g of water and 50 g of toluene were added for layer separation. To the water layer was added 45 g of concentrated hydrochloric acid, and the mixture was cooled to room temperature. The resulting crystal was filtered and dried to yield 28.7 g of 2,5-dichlorophenylthioglycolic acid. Its melting point was 129° to 131° C., and the yield was 60.5%. The results are given in Table 2.

後処理

  1. customTo a 500 ml flask equipped with a thermometer, a condenser and a stirrer
  2. distillationThen, after distilling off the solvent, 300 g of water and 50 g of toluene
  3. additionwere added for layer separation
  4. additionTo the water layer was added 45 g of concentrated hydrochloric acid
  5. filtrationThe resulting crystal was filtered
  6. customdried

出典と根拠

ORDレコード
ord-a8496bce6d5e4e34bf39273275a81065
出典データセット
uspto-grants-1993_05
特許番号
US05210291

関連ノート

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