1,2-Dichloroethane → Methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate

HRID 62721Notes

Reaction equation

HRID 62721 reaction equation
BrC1C=C(N[C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:14])C=C(Br)C=1OCC.C(Cl)CCl.[CH2:29]([O:31][C:32]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[C:43]([F:46])([F:45])[F:44])[CH3:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:29]([O:31][C:32]1[C:33]([C:43]([F:44])([F:45])[F:46])=[CH:34][C:35]([NH:36][C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:14])=[CH:37][C:38]=1[C:39]([F:40])([F:41])[F:42])[CH3:30]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 67041561HCID 67041561, compoundHCID 86666596HCID 86666596, compound

Product 1

HCID 86666597Methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoateYield 28%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(Methoxycarbonyl)benzoic acid (4) (246 mg, 1.37 mmol) was dissolved in DCM (15 mL) and treated with EDC (654 mg, 3.41 mmol) and DMAP (33 mg, 273 μmol). The resultant mixture was stirred at RT for 15 min. 4-Ethoxy-3,5-bis(trifluoromethyl)aniline (3) (360 mg, 1.32 mmol) was added and the resultant mixture was stirred at RT for 20 h. The mixture was diluted with EtOAc and washed three times with 1 M HCl and then three times with NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (10% EtAOc in isohexane) to afford methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate (5) (150 mg, 28%): m/z 436 [M+H]+ (ES+).

Workup

  1. washwashed three times with 1 M HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by silica gel chromatography (10% EtAOc in isohexane)

Sources & evidence

ORD record
ord-42b4bc701d9e4e08bbfe555360d54a48
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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