Ammonium Hydroxide → Methyl[3,5-bis(trifluoromethyl)benzyl][2-cyano-5-(trifluoromethyl)benzyl]carbamate

HRID 17083Notes

Reaction equation

HRID 17083 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25](C(F)(F)F)[CH:26]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1I)[C:8](=[O:11])[O:9][CH3:10].[C:33]([Cu])#[N:34].[NH4+].[OH-]>CN(C=O)C>[CH3:10][O:9][C:8](=[O:11])[N:7]([CH2:6][C:5]1[CH:24]=[C:25]([C:2]([F:32])([F:31])[F:1])[CH:26]=[C:3]([C:2]([F:31])([F:1])[F:32])[CH:4]=1)[CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:33]#[N:34]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 59343876Methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamateHCID 178418546HCID 178418546, compound

Product 1

HCID 87540861Methyl[3,5-bis(trifluoromethyl)benzyl][2-cyano-5-(trifluoromethyl)benzyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 5 dissolved in DMF (1.5 mL) was added CuCN (20 mg, 0.22 mmol) and the resultant mixture was heated at 100° C. for 16 h. The reaction was cooled to room temperature, poured into NH4OH (10 mL) and extracted with EtOAC (4×30 mL). The combined organic extracts were washed with H2O and brine (10 mL each), dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (0 to 25% EtOAc/hexanes) afforded the title compound as a colorless oil. LCMS=485 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.81 (s, 1H), 7.78 (d, J=7.7 Hz, 1H), 7.67-7.31 (m, 4H), 4.82 (br s, 2H), 4.72 (s, 2H), 3.91 (s, 3H).

Workup

  1. extractionextracted with EtOAC (4×30 mL)
  2. washThe combined organic extracts were washed with H2O and brine (10 mL each)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (0 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-17199744cbc54100870e490b3d461b1f
Source dataset
uspto-grants-2010_06
Patent number
US07737295B2

Reaction notes

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