Water → HCID 11305162, compound

HRID 1267511Notes

Reaction equation

HRID 1267511 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][NH:7][C:8]([C:10]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:9].[CH3:31]N(C)C=O.CI.O>[Cl-].[Na+].O.C(Cl)Cl>[F:1][C:2]([F:29])([F:30])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][N:7]([CH3:31])[C:8]([C:10]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11475738HCID 11475738, compound

Product 1

HCID 11305162HCID 11305162, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 0.63 g (1.50 mmol) biphenyl-2-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide in 10 ml N,N-dimethylformamide 0.08 g (1.98 mmol) sodiumhydride (60% dispersion in mineral oil) was added and the reaction mixture was stirred for 1 hr. After the addition of 0.15 ml (2.4 mmol) methyl iodide at 0°, the reaction mixture was stirred for 3 hrs. at RT. The reaction mixture was distributed between 50 ml H2O, 50 ml brine and 50 ml CH2Cl2. The phases were separated, the aqueous layer washed twice with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, ethyl acetate/CH2Cl2 15:1) to give 0.50 g (76%) biphenyl-2-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as colorless solid, m.p. 97-88°.

Workup

  1. stirringthe reaction mixture was stirred for 3 hrs
  2. customat RT
  3. customThe phases were separated
  4. washthe aqueous layer washed twice with 50 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, ethyl acetate/CH2Cl2 15:1)

Sources & evidence

ORD record
ord-c0eee41658f9442496d4272d4c1b1df6
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

Loading…