Hydrochloric Acid → N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide

HRID 256769

反応式

HRID 256769 の反応式
[CH3:1][NH:2][CH:3]=[O:4].C(N(CC)CC)C.ClC(OC(Cl)=O)(Cl)Cl.[O:20]([C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](O)=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S(Cl)(Cl)=O.Cl>C1(C)C=CC=CC=1.O.CC(C)=O>[CH3:1][NH:2][C:3](=[O:4])[C:29]([C:28]1[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:30]

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10426DiphosgeneHCID 24386Thionyl ChlorideHCID 31254N-MethylformamideHCID 752372-Phenoxybenzoic acid

生成物 1

HCID 11780091N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide収率 61%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
10 °C

実験手順

N-Methylformamide (2.36 g, 40.0 mmol) and triethyl amine (8.08 g, 80.0 mmol) were dissolved in toluene (40 ml). Trichloromethylchloroformate (3.96 g, 20.0 mmol) was added dropwise slowly under ice-cooling while maintaining the inner temperature at 10° C. or lower. The mixture was stirred at the same temperature for 1 hour. A large amount of insoluble materials were precipitated. To the mixture was added 2-phenoxybenzoyl chloride which was prepared from 2-phenoxybenzoic acid (4.28 g, 20.0 mmol) and thionyl chloride (2.86 g, 24.0 mmol). The resulting mixture was stirred at bath temperature of 40° to 50° C. for 26 hours. 5N-Hydrochloric acid (12 ml) and acetone (20 ml) were added, and the mixture was stirred for 12 hours. Water was added to the mixture, which was then extracted with toluene and purified by column chromatography on silica gel to obtain the title compound (3.11 g, Yield: 61.0%).

後処理

  1. temperaturecooling
  2. customA large amount of insoluble materials were precipitated
  3. additionTo the mixture was added 2-phenoxybenzoyl chloride which
  4. stirringThe resulting mixture was stirred at bath temperature of 40° to 50° C. for 26 hours
  5. stirringthe mixture was stirred for 12 hours
  6. extractionwas then extracted with toluene
  7. custompurified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-fce1158198784bd78811a8322f558a03
出典データセット
uspto-grants-1993_11
特許番号
US05258551

関連ノート

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