Ammonia → 3-[4-(6-Methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)phenyl]-2-methylthiopropionic Amide

HRID 1358570Notes

Reaction equation

HRID 1358570 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:24])[C:21](O)=[S:22])=[CH:15][CH:14]=3)[N:8]([CH3:25])[C:7]=2[CH:26]=1.O1CCCC1.ClC(OCC)=O.[NH3:38]>C(N(CC)CC)C.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:19][CH:20]([CH3:24])[C:21]([NH2:38])=[S:22])=[CH:17][CH:18]=3)[N:8]([CH3:25])[C:7]=2[CH:26]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 178487958HCID 178487958, compound

Product 1

HCID 181850573-[4-(6-Methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)phenyl]-2-methylthiopropionic Amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 3-[4-(6-methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)phenyl]-2-methylthiopropionic acid (1.1 g), tetrahydrofuran (15 ml) and dimethylformamide (15 ml) were added successively triethylamine (0.82 ml) and ethyl chloroformate (0.28 ml). The mixture was stirred at room temperature for 30 minutes. After addition of aqueous ammonia solution (5 ml, 28%) the mixture was stirred at room temperature for 15 minutes and allowed to stand overnight. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with ethyl acetate and then recrystallized from a mixture of ethanol and ethyl acetate to afford the title compound (0.45 g, mp 204-206° C.).

Workup

  1. stirringwas stirred at room temperature for 15 minutes
  2. waitto stand overnight
  3. customThe solvent of the reaction mixture was evaporated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with ethyl acetate
  9. customrecrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-8dc462be78d64fe580336b0523fd4be6
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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