Dimethylformamide dimethyl acetal → N'-[4-Bromo-2-(4,4dimethyl-cyclohex-1-enyl)-phenyl]-N,N-dimethyl-formamidine

HRID 456001Notes

Reaction equation

HRID 456001 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]2[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][CH:10]=2)[CH:3]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:19][N:20]([CH3:22])[CH3:21])=[C:4]([C:9]2[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][CH:10]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 591285714-Bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenylamine

Product 1

HCID 57666559N'-[4-Bromo-2-(4,4dimethyl-cyclohex-1-enyl)-phenyl]-N,N-dimethyl-formamidineYield 73%

Procedure

A solution of 4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenylamine (as prepared in Example 1, step (a), 3.0 g, 10 mmol) in N,N-dimethylformamide dimethyl acetal (20 mL) was heated at reflux under Ar for 48 h. The solvent was removed under reduced pressure and the residue was purified on silica gel (5-20% EtOAc/hexane) to obtain the title compound (2.6 g, 73%). 1H-NMR (CDCl3; 400 MHz): δ 7.36 (s, 1H), 7.23-7.21 (m, 2H), 6.65 (d, 1H, J=8.0 Hz), 5.64 (m, 1H), 2.97 (s, 6H), 2.37 (m, 2H), 1.95 (m, 2H), 1.44 (m, 2H), 0.99 (s, 6H).

Workup

  1. temperatureat reflux under Ar for 48 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified on silica gel (5-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-d3cd4931807b4868b908a8e69984f671
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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