Hexane → Methyl (n-(5-chloro-2-propionylphenyl)-N-phenylcarbamoyl)formate

HRID 1887789

反応式

HRID 1887789 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1.Cl[C:20](=[O:25])[C:21]([O:23][CH3:24])=[O:22].CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:24][O:23][C:21](=[O:22])[C:20]([N:12]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[C:8](=[O:11])[CH2:9][CH3:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:25]

参加物

6

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 79846Methyl chloroglyoxylateHCID 708166141-(4-Chloro-2-phenylamino-phenyl)-propan-1-one

生成物 1

HCID 70816656Methyl (n-(5-chloro-2-propionylphenyl)-N-phenylcarbamoyl)formate収率 87.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a solution of 1-(4-chloro-2-phenylamino-phenyl)-propan-1-one (13.0 g, 50.2 mmol) in toluene (150 mL) was added methyl chlorooxoacetate (42.86 g, 350.0 mmol) at room temperature under nitrogen. The reaction mixture was heated at reflux at 110° C. for 16 hr. Completion of the reaction was monitored by silica TLC (mobile phase; hexane:ethyl acetate=1:1; Rf=0.5). The reaction mixture was concentrated under vacuum to afford 15.2 g (87.6% crude yield) of N-(5-chloro-2-propionyl-phenyl)-N-phenyl-oxalamic acid methyl ester. The crude product was used in the next step without further purification.

後処理

  1. temperatureThe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated under vacuum

出典と根拠

ORDレコード
ord-d8fb32f5730d4ecaa7e2e137302bf31b
出典データセット
uspto-grants-2013_08
特許番号
US08501732B2

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