Acetic Anhydride → HCID 11983398, compound

HRID 2262734Notes

Reaction equation

HRID 2262734 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([CH2:21][NH2:22])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[CH:10][CH:11]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>ClCCl>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11983378HCID 11983378, compound

Product 1

HCID 11983398HCID 11983398, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of C-[1-(3-thiazol-2-yl-phenyl)-1H-benzoimidazol-5-yl]-methylamine (0.70 g, 2.3 mmol) in dichloromethane (30 ml) was added acetic anhydride (2.4 ml, 2.5 mmol) dropwise with stirring. After the addition, stirring was continued for 30 min and the reaction mixture was washed twice with saturated, aqueous sodium bicarbonate and once with water. The organic phase was dried over sodium sulfate and concentrated in vacuo. The concentrate was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane, methanol and ammonia (9:1:0.1 v/v/v). This afforded the desired product (0.52 g, 65%). Mp. 156.4° C.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. washthe reaction mixture was washed twice with saturated, aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe concentrate was purified by column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane, methanol and ammonia (9:1:0.1 v/v/v)

Sources & evidence

ORD record
ord-d7b3db336e1b4f63b5ebf1aceb1ab988
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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