Acetic Acid → 1-(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)benzyl)urea

HRID 499939Notes

Reaction equation

HRID 499939 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[CH2:15][NH2:16].[O-:19][C:20]#[N:21].[K+].C(O)(=O)C>C1COCC1.O.C(OCC)(=O)C>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:6]=1[CH2:15][NH:16][C:20]([NH2:21])=[O:19]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 44235013(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)phenyl)methanamine

Product 1

HCID 442352571-(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)benzyl)urea

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 1B (9.0 g, 35 mmol), potassium cyanate (4.2 g, 52 mmol), and glacial acetic acid (3.1 mL, 52 mmol) in THF (70 mL) and water (7 mL) was stirred at 60° C. for 2 hours, diluted with ethyl acetate, and sequentially washed with saturated aqueous NaHCO3 and brine. The organic layer was concentrated under reduced pressure to provide the title compound. 1H-NMR (DMSO-d6) δ 7.41 (m, 3H), 4.69 (brs, 1H), 4.45 (d, 2H), 4.37 (brs, 2H), 2.64 (ddd, 2H), 1.45 (ddd, 2H), 0.99 (s, 9H).

Workup

  1. washsequentially washed with saturated aqueous NaHCO3 and brine
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4aba15091225447dad193c4ab4a5006c
Source dataset
uspto-grants-2010_08
Patent number
US07767705B2

Reaction notes

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