Acetic Acid → 1-(3-Bromophenyl)-1-methylethylamine

HRID 1785453Notes

Reaction equation

HRID 1785453 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:11]C(=O)CCl)([CH3:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.NC(N)=S.C(O)(=O)C.O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:11])([CH3:9])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2723790ThioureaHCID 57593166N-(2-(3-bromophenyl)propan-2-yl)-2-chloroacetamide

Product 1

HCID 130256661-(3-Bromophenyl)-1-methylethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of N-[1-(3-bromo-phenyl)-1-methyl-ethyl]-2-chloro-acetamide (1.0 g, 3.5 mmol), thiourea (0.32 g, 4.2 mmol), acetic acid (1.5 mL) in ethanol (7 mL) was heated to reflux for 10 h and brought to room temperature. Water was added to the mixture until a precipitate was formed which was filtered. The filtrate was made basic pH 7-8 with 15% NaOH. The product was extracted with ethyl acetate and concentrated to afford a yellow solid. M+1=214.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 h
  3. custombrought to room temperature
  4. customwas formed which
  5. filtrationwas filtered
  6. extractionThe product was extracted with ethyl acetate
  7. concentrationconcentrated
  8. customto afford a yellow solid

Sources & evidence

ORD record
ord-c93c2c43beef47f48b7d8aba95b9eaec
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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