2-Chloroaniline → HCID 58970390、化合物

HRID 1678044ノート

反応式

HRID 1678044 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].ClOC(C)(C)C.[CH3:15][S:16][CH:17]([C:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=1)[CH3:18].C[O-].[Na+]>ClCCl.O.CO>[CH3:15][S:16][C:17]([C:19]1[N:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[N:24]=1)([C:5]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[C:3]=1[NH2:4])[CH3:18]

参加物

8

反応物 4

HCID 72402-ChloroanilineHCID 521297Tert-Butyl hypochloriteHCID 10942334Sodium MethoxideHCID 58970391HCID 58970391、化合物

生成物 1

HCID 58970390HCID 58970390、化合物収率 90%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-65 °C

実験手順

2-Chloroaniline 7 g (32.7 mmol) was dissolved in dichloromethane 100 ml and the solution was cooled to −65° C. To the solution a solution of t-butyl hypochlorite 3.55 g (32.7 mmol) in dichloromethane 10 ml was added dropwise and the solution was stirred at the same temperature for 10 minutes. Then a solution of 2-(1-methylthioethyl)-4,6-dimethoxypyrimidine in dichloromethane was added thereto dropwise and the solution was stirred at the same temperature for 1 hour. After a methanol solution of sodium methoxide 12.6 g (65.3 mmol) had been added dropwise and the mixed solution had been stirred at the same temperature for 10 minutes, the reaction solution was stirred until it came to room temperature. The reaction solution was poured into water and extracted with dichloromethane. The solvent was distilled off and the residue was purified with column chromatography (hexane/ethyl acetate=5/1) to obtain 2-{1-methylthio-1-(2-amino-3-chlorophenyl)ethyl}-4,6-dimethoxypyrimidine 10.0 g (90%).

後処理

  1. stirringdropwise and the solution was stirred at the same temperature for 1 hour
  2. stirringthe mixed solution had been stirred at the same temperature for 10 minutes
  3. stirringthe reaction solution was stirred until it
  4. customcame to room temperature
  5. extractionextracted with dichloromethane
  6. distillationThe solvent was distilled off
  7. customthe residue was purified with column chromatography (hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-ab3365f631b4493c95169466faad38ad
出典データセット
uspto-grants-2011_08
特許番号
US08008484B2

反応ノート

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