Water → HCID 53985945, compound

HRID 581977Notes

Reaction equation

HRID 581977 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:27]=[CH:26][C:10]2[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][N:21]=4)[CH:15]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1)=[O:6].O>CO>[O:6]1[C:5]([C:7]2[CH:27]=[CH:26][C:10]3[N:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]5[CH:25]=[CH:24][N:23]=[CH:22][N:21]=5)[CH:15]=4)[CH:12]=[N:13][C:9]=3[CH:8]=2)=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 962WaterHCID 54142092HCID 54142092, compound

Product 1

HCID 53985945HCID 53985945, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(3dimethylamino-1-oxo-2-propen-1-yl)-1-(3-(4-pyrimidinyl)phenyl)benzimidazole (307 mg) and NH2OH,HCl (135 mg, 2.5 equivalents) in methanol (14 ml) was stirred at 80° C. for 2 hours. After cooling the mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried, and concentrated under reduced pressure. The residue was chromatographied (CH2Cl2 -methanol 40:1 (v/v)) to give 5-(5-isoxazolyl)-1-(3-(4-pyrimidinyl)phenyl)benzimidazole (226 mg, 80%).

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-663cc99fc6554b81a04d168e9f2bea8c
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

Loading…