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

HRID 2410075Notes

Reaction equation

HRID 2410075 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-6d09b19ee7a84003bd22767b2fa63768
Source dataset
uspto-grants-2014_08
Patent number
US08815930B2

Reaction notes

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