Hydrogen Peroxide → Methyl 4-carbamoyl-2-chlorobenzoate

HRID 1978201ノート

反応式

HRID 1978201 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 53785786Methyl 4-carbamoyl-2-chlorobenzoate収率 498%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0df37480ccc4460abd23ad8bb871975f
出典データセット
uspto-grants-2001_05
特許番号
US06235900B1

反応ノート

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