Methyl dichloroacetate → 2-Amino-5-(2-(3-chlorophenyl)ethyl)-4-thiazolecarboxylic acid, methyl ester

HRID 324486

反応式

HRID 324486 の反応式
[CH3:1][O-].[Na+].[Na].[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]([CH3:15])C=O)[CH:9]=[CH:10][CH:11]=1.Cl[CH:17](Cl)[C:18]([O:20][CH3:21])=[O:19].[NH2:23][C:24]([NH2:26])=[S:25]>CO.C(OCC)C>[NH2:23][C:24]1[S:25][C:1]([CH2:15][CH2:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[CH:7]=2)=[C:17]([C:18]([O:20][CH3:21])=[O:19])[N:26]=1

参加物

8

反応物 5

HCID 8315Methyl dichloroacetateHCID 2723790ThioureaHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22003664HCID 22003664、化合物

生成物 1

HCID 1317225262-Amino-5-(2-(3-chlorophenyl)ethyl)-4-thiazolecarboxylic acid, methyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

A solution of sodium methoxide (made from 1.43 g of sodium in dry methanol (20 ml) was added dropwise to a stirred solution of 2-(3-chlorophenyl)propanal (10.4 g) and methyl dichloroacetate (6.4 ml) in diethyl ether (30 ml) at 0° C. under nitrogen. After 1 h the mixture was quenched with brine and the product extracted into diethyl ether. The organic phase was collected, dried (MgSO4) and evaporated under reduced pressure to leave a yellow oil. The oil and thiourea (4.72 g) were dissolved in methanol (40 ml) and the mixture set at reflux for 4 h. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was separated, washed with water, collected, dried (MgSO4) and solvent evaporated under reduced pressure to leave a brown solid. The solid was triturated with isohexane and ethyl acetate mixtures and filtered to leave the subtitle product.

後処理

  1. customAfter 1 h the mixture was quenched with brine
  2. extractionthe product extracted into diethyl ether
  3. customThe organic phase was collected
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto leave a yellow oil
  7. temperatureat reflux for 4 h
  8. customThe solvent was removed under reduced pressure
  9. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  10. customThe organic phase was separated
  11. washwashed with water
  12. customcollected
  13. dry with materialdried (MgSO4) and solvent
  14. customevaporated under reduced pressure
  15. customto leave a brown solid
  16. customThe solid was triturated with isohexane and ethyl acetate mixtures
  17. filtrationfiltered

出典と根拠

ORDレコード
ord-dddf062f82964e548e8b596073e36a2a
出典データセット
uspto-grants-2001_04
特許番号
US06218376B1

関連ノート

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