Hydrogen Peroxide → Methyl 4-carbamoyl-2-chlorobenzoate

HRID 1978201노트

반응식

HRID 1978201 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[Cl:12].C(=O)([O-])[O-:15].[K+].[K+].OO>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH2:11])=[O:15])=[CH:6][C:5]=1[Cl:12]

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 53845357Methyl 2-chloro-4-cyanobenzoate

생성물 1

HCID 53785786Methyl 4-carbamoyl-2-chlorobenzoate수율 498%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of 2-chloro-4-cyano benzoic acid methyl ester (12.4 g, 63.4 mmol) and potassium carbonate (1.3 g, 9.4 mmol) in dimethylsulfoxide (40 mL) was treated dropwise under cooling with 30% hydrogen peroxide (7.6 mL). The mixture was allowed to warm to room temperature and stirred overnight. The solution was quenched with water and the resulting precipitate collected by filtration. The crude material was dissolved in dichloromethane and absorbed on a silica gel Merck-60 flash column. Elution with a dichloromethane-methanol gradient (from 98:2 to 90:10) provided the title compound (10 g) as a white solid, m.p. 154-156° C.

후처리

  1. additionwas treated dropwise
  2. customThe solution was quenched with water
  3. filtrationthe resulting precipitate collected by filtration
  4. dissolutionThe crude material was dissolved in dichloromethane
  5. customabsorbed on a silica gel Merck-60 flash column
  6. washElution with a dichloromethane-methanol gradient (from 98:2 to 90:10)

출처 및 근거

ORD 기록
ord-0df37480ccc4460abd23ad8bb871975f
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235900B1

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