Triethylamine → Methyl 3-(3-chlorobenzamido)benzoate

HRID 970268ノート

反応式

HRID 970268 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[NH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])=[O:6]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 78274Benzoic acid, 3-amino-, methyl ester

生成物 1

HCID 723590Methyl 3-(3-chlorobenzamido)benzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

To a solution of 15.1 gm (86 mmol) of 3-chlorobenzoyl chloride in 70 mL of dichloromethane was added 10.0 gm (66 mmol) of methyl 3-aminobenzoate. Triethylamine (9.38 gm, 13 mL, 93 mmol) was then added slowly to the mixture. After the addition was complete, the solution was warmed to 45° C. and stirred overnight. Ice was added to the solution to quench excess benzoyl chloride. After one hour, the layers were separated. The organic fraction was washed with 5% aqueous hydrochloride acid, saturated sodium bicarbonate, and finally with saturated sodium chloride solution. The dichloromethane solution was dried over magnesium sulfate. The drying agent was filtered off, and the solvent was removed by rotoevaporation to give the desired methyl 3-(3-chlorobenzamido)benzoate. 1H NMR (CDCl3): δ3.91 (s, 3H), 7.61 (d of t, 1H), 7.78 (d of t, 1H, 7.87 (d of t, 1H), 8.40 (d of d, 1H), and 8.94 ppm (br s, 1H). MS m/z: 290.0 (M+H).

後処理

  1. additionAfter the addition
  2. additionIce was added to the solution
  3. customto quench excess benzoyl chloride
  4. waitAfter one hour
  5. customthe layers were separated
  6. washThe organic fraction was washed with 5% aqueous hydrochloride acid, saturated sodium bicarbonate
  7. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. customthe solvent was removed by rotoevaporation

出典と根拠

ORDレコード
ord-22433ec5d7a044b7ba5bff6f93d010ed
出典データセット
uspto-grants-2007_12
特許番号
US07312181B2

反応ノート

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