Triethylamine → 4-Benzyloxy-N3-[3,5-bis(trifluoromethyl)phenyl]-N1,N1-dimethylisophthalamide

HRID 644422Notes

Reaction equation

HRID 644422 reaction equation
C[CH2:2][N:3]=[C:4]=NCCCN(C)C.Cl.[CH2:13]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][C:22]=1[C:30]([NH:32][C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=1)=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.CNC.C(N(CC)CC)C>O1CCCC1.O>[CH2:13]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:3]([CH3:4])[CH3:2])=[O:26])=[CH:23][C:22]=1[C:30]([NH:32][C:33]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=1)=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866026784-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]isophthalamic acid

Product 1

HCID 865955374-Benzyloxy-N3-[3,5-bis(trifluoromethyl)phenyl]-N1,N1-dimethylisophthalamideYield 64.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

WSC.HCl (95 mg, 0.50 mmol) was added to a solution of 4-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]isophthalamic acid (242 mg, 0.50 mmol), dimethylamine hydrochloride (41 mg, 0.50 mmol) and triethylamine (51 mg, 0.50 mmol) in tetrahydrofuran (5 mL) under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with diluted hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by chromatography on silica gel (hexane:ethyl acetate=1:4) to give the title compound (165 mg, 64.9%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with diluted hydrochloric acid, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by chromatography on silica gel (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-e41b4908509e4158801213d302a2f3be
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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