Benzyl Bromide → HCID 22631537, compound

HRID 1840435Notes

Reaction equation

HRID 1840435 reaction equation
[C:1]([S:4][C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[CH:11][S:10][C:9]=12)(=O)[CH3:2].C[O-].[Na+].CO.C(Br)[C:19]1[CH:24]=[CH:23]C=[CH:21][CH:20]=1.[Cl-].[NH4+]>CO>[CH2:1]([S:4][C:5]1[N:6]=[CH:7][N:8]2[CH:12]=[CH:11][S:10][C:9]=12)[C:2]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 22631663HCID 22631663, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 22631537HCID 22631537, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 396 mg of 7-acetylthioimidazo[5,1-b]thiazole in 2 ml of methanol was cooled in ice. A 1.018 M sodium methoxide/methanol solution (2.16 ml) was added to the cooled solution, and the mixture was stirred for 30 min. Benzyl bromide (0.262 ml) was added thereto, and the mixture was stirred at that temperature for 2 hr. An aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine twice, and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residue was purified by column chromatography on silica gel (dichloromethane:methanol=30:1) to prepare 419 mg of 7-benzylthioimidazo[5,1-b]thiazole.

Workup

  1. stirringthe mixture was stirred at that temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate twice
  3. washThe organic layer was washed with brine twice
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation
  6. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol=30:1)
  7. customto prepare 419 mg of 7-benzylthioimidazo[5,1-b]thiazole

Sources & evidence

ORD record
ord-b75e533d0ffa427395894507916ecc93
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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