2-Bromopropane → HCID 13534679, compound

HRID 46762Notes

Reaction equation

HRID 46762 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[S:19])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH:24](Br)([CH3:26])[CH3:25]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([S:19][CH:24]([CH3:26])[CH3:25])[NH:11][C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 113577395-(4-Fluorophenyl)-4-pyridin-4-yl-1H-imidazole-2-thiolHCID 178418361HCID 178418361, compound

Product 1

HCID 13534679HCID 13534679, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 8.0 g of 4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazole-2-thione in 100 ml of dimethylformamide was added 1.56 g of sodium hydride (50% in mineral oil). The mixture was stirred until the evolution of hydrogen ceased. At this point 3.9 g of isopropyl bromide was added with a syringe. After stirring for 3 hours the mixture was poured into water, filtered and air dried. Trituration with ether, filtering and drying gave 5.73 g. Recrystallizing a 3.0 g sample from ethanol gave 1.4 g of the title compound, m.p. 263°-264°.

Workup

  1. filtrationfiltered
  2. customair dried
  3. filtrationTrituration with ether, filtering
  4. customdrying
  5. customgave 5.73 g
  6. customRecrystallizing a 3.0 g sample from ethanol

Sources & evidence

ORD record
ord-e668321342e74530b0e5ede37fe96fb7
Source dataset
uspto-grants-1979_11
Patent number
US04175127

Reaction notes

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