Benzyl Bromide → HCID 20435309, compound

HRID 1154337Notes

Reaction equation

HRID 1154337 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([N:9]([CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:10]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2842773N-[3-(1H-Imidazol-1-yl)propyl]-2-thiophenecarboxamide

Product 1

HCID 20435309HCID 20435309, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.7 g. of N-[3-(1H-imidazol-1-yl)propyl]-2-thiophene carboxamide, 40 ml. of dimethylformamide, and 0.96 g. of 50% sodium hydride in oil was stirred for 2 hours and 2.62 g. of benzyl bromide was added. The mixture was stirred for 24 hours, concentrated to remove the dimethyl formamide, diluted with water and methylene chloride, and the layers separated. The organic layer was washed with water, dried over magnesium sulfate, and concentrated. The oil was twice washed with hexane and again concentrated. The desired product was obtained as an oil.

Workup

  1. additionA mixture of 4.7 g
  2. concentrationconcentrated
  3. customto remove the dimethyl formamide
  4. additiondiluted with water and methylene chloride
  5. customthe layers separated
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. washThe oil was twice washed with hexane
  10. concentrationagain concentrated

Sources & evidence

ORD record
ord-f465654bea944314bbb3b413b612107f
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Reaction notes

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