2-Bromo-4'-nitroacetophenone → HCID 824462, compound

HRID 1595274Notes

Reaction equation

HRID 1595274 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=O.[CH3:14][N:15]([CH3:19])[C:16]([NH2:18])=[S:17]>C(O)(C)C.CCOC(C)=O>[CH3:14][N:15]([CH3:19])[C:16]1[S:17][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[N:18]=1

Participants

5

Reactant 2

HCID 668402-Bromo-4'-nitroacetophenoneHCID 30341921,1-Dimethyl-2-thiourea

Product 1

HCID 824462HCID 824462, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4′-nitroacetophenone (4.42 g, 18.1 mmol), N,N,-dimethylthiourea (3.77 g, 36.2 mmol) in isopropanol (60 mL) was heated at reflux for 45 min. The cooled reaction mixture was diluted with EtOAc. The solution was washed with saturated aqueous NaHCO3, H2O and brine, dried (MgSO4) and concentrated under reduced pressure to give N,N-dimethyl-4-(4-nitrophenyl)-2-thiazolamine (2.92 g, 65% yield) as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ8.24 (d, J=8.8 Hz, 2H), 8.11 (d, J=8.8 Hz, 2H), 7.56 (s, 1H), 3.11 (s, 6H); MS (FAB) m/z 250 (MH)+.

Workup

  1. temperatureat reflux for 45 min
  2. customThe cooled reaction mixture
  3. washThe solution was washed with saturated aqueous NaHCO3, H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d16b1946186d4815b663d994d819f8b0
Source dataset
uspto-grants-2001_09
Patent number
US06288091B1

Reaction notes

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