Acetic Acid → 1-(3-bromophenyl)-2-methylpropan-2-amine

HRID 1866507Notes

Reaction equation

HRID 1866507 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:12]C(=O)CCl)([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.NC(N)=S.C(O)(=O)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH2:12])([CH3:10])[CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723790ThioureaHCID 58907445N-[2-(3-Bromophenyl)-1,1-dimethylethyl]-2-chloroacetamide

Product 1

HCID 230877171-(3-bromophenyl)-2-methylpropan-2-amineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[2-(3-bromophenyl)-1,1-dimethylethyl]-2-chloroacetamide (Preparation 30) (32.0 g, 105 mmol), thiourea (9.60 g, 126 mmol) and acetic acid (50 ml) in ethanol (250 ml) was heated to reflux overnight. The reaction mixture was cooled to room temperature and filtered, the filtrate was concentrated in vacuo and basified using aqueous sodium hydroxide solution (1M, 450 ml). The product was extracted with dichloromethane (2×500 ml) and the combined organics washed with brine (50 ml), dried (sodium sulfate) and the solvent removed in vacuo to afford the title compound as a black oil (23 g). 1H NMR (400 MHz, CDCl3) δ=7.36-7.32 (2H, m), 7.16-7.08 (2H, m), 2.62 (2H, s), 1.84 (2H, bs), 1.12 (6H, s). LRMS (electrospray) m/z 228 [M+H]+

Workup

  1. temperatureto reflux overnight
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. extractionThe product was extracted with dichloromethane (2×500 ml)
  5. washthe combined organics washed with brine (50 ml)
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-eec3274ba51e4f86a0049f54c46a4e4c
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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