Triethylamine → Methyl 3-(3-trifluoromethylbenzamido)benzoate

HRID 970271Notes

Reaction equation

HRID 970271 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[NH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 850566Methyl 3-(3-trifluoromethylbenzamido)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 17.9 gm (86 mmol) of 3-trifluoromethylbenzoyl 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-trifluoromethylbenzamido)benzoate. 1H NMR (CDCl3): δ3.92 (s. 3H), 7.52 (t, 1H), 7.74 (t, 1H), 7.80 (m, 1H), 7.92 (m, 1H), 7.96 (m, 1H), 8.21 (d, 1H), 8.26 (s, 1H), 8.43 (s, 1H), and 9.07 (br s, 1H). MS m/z: 324.0 (M+H).

Workup

  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

Sources & evidence

ORD record
ord-520eb1f4c4584c81b11fb7d362525d17
Source dataset
uspto-grants-2007_12
Patent number
US07312181B2

Reaction notes

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