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

HRID 256769

반응식

HRID 256769 반응식
[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]

참가 물질

10

반응물 6

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

생성물 1

HCID 11780091N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide수율 61%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
10 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-fce1158198784bd78811a8322f558a03
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258551

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