Water → Ethyl 4-[(2-methylbenzoyl)amino]benzoate

HRID 439945

反応式

HRID 439945 の反応式
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].C(N(CC)CC)C.O>ClCCl>[CH3:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1)=[O:17]

参加物

6

反応物 4

HCID 962WaterHCID 2337BenzocaineHCID 8471TriethylamineHCID 702762-Methylbenzoyl chloride

生成物 1

HCID 689910Ethyl 4-[(2-methylbenzoyl)amino]benzoate収率 76.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 43.42 g of ethyl 4-aminobenzoate and 40.8 g of 2-methylbenzoyl chloride in 150 ml of dichloromethane is cooled in an ice bath and 26.56 g of triethylamine is added dropwise. After the addition, the solution is stirred at room temperature overnight. The mixture is poured into water and the organic layer separted. The organic layer is washed with water, 1N HCl, 1M NaHCO3 and dried over Na2SO4. The solvent is removed and the solid slurried with ethyl acetate and filtered to give 57 g of ethyl 4-[(2-methylbenzoyl)amino]benzoate as crystals, m.p. 110°-115° C. A mixture of 50.7 g of the preceding compound in 280 ml of ethyl alcohol and 55 ml of 10N NaOH is refluxed for 5 minutes. The mixture is cooled to room temperature, diluted with 200 ml of water and acidified with concentrated hydrochloric acid (pH 1-2). The mixture is filtered and the solid washed with water and dried to give 51 g of the desired product as white crystals, m.p. 270°-275° C.

後処理

  1. temperatureis cooled in an ice bath
  2. additionAfter the addition
  3. washThe organic layer is washed with water, 1N HCl, 1M NaHCO3
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed
  6. filtrationthe solid slurried with ethyl acetate and filtered

出典と根拠

ORDレコード
ord-f97a06b5a94d40caa417a658a5c68c65
出典データセット
uspto-grants-1996_05
特許番号
US05516774

関連ノート

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