Triethylamine → 3-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester

HRID 852555ノート

反応式

HRID 852555 の反応式
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH2:13])[CH:6]=1.CCN(CC)CC.[Cl:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl.CCOC(C)=O>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH:13][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][Cl:22])[CH:6]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 693575963-Amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride

生成物 1

HCID 693577003-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester収率 103.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride (D62) (0.13 g, 0.556 mmol, 1 equiv) in dry CH2Cl2 (2 ml) at 0° C. was added NEt3 (193 ml, 1.39 mmol, 2.5 equiv) then 4-chlorobutyryl chloride (69 ml, 0.612 mmol, 1.1 equiv), dropwise, over 2 min. The resulting solution was stirred at 0° C. for 15 min then at room temperature for 30 min. The solution was then diluted with AcOEt, washed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo to give 3-(4-chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester (D64) (173 mg, 103%) as pale yellow crystals. [M+H]+=302.0, RT=3.20 min

後処理

  1. waitat room temperature for 30 min
  2. washwashed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6ed46d440efe4513ae9c5a11f1d3fda9
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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