Triethylamine → Methyl 3-(3-chlorobenzamido)benzoate

HRID 970268노트

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HRID 970268 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 723590Methyl 3-(3-chlorobenzamido)benzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-22433ec5d7a044b7ba5bff6f93d010ed
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312181B2

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