Water → HCID 178441449, compound

HRID 1655448Notes

Reaction equation

HRID 1655448 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[C:8]2[CH:25]=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[N-:29]=[N+:30]=[N-:31].[Na+].[Cl-].[NH4+].O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:31][N:30]=[N:29][N:24]=3)=[CH:13][CH:12]=2)[C:8]2[CH:25]=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 197921082-Butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole

Product 1

HCID 178441449HCID 178441449, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]benzimidazole (1.8 g), sodium azide (0.98 g) and ammonium chloride (0.80 g) was stirred in DMF (6 ml) at 110° C. for 5 days, while supplementing sodium azide (1.6 g), ammonium chloride (1.3 g) and DMF (5 ml) to the reaction system. To the reaction mixture were added water and ethyl acetate, and precipitating crystals were collected by filtration. The organic layer of the filtrate was washed with water, dried and concentrated under reduced pressure to give crude crystals. These crystals were combined with the crystals obtained previously, this was followed by recrystallization from ethyl acetate - methanol to afford colorless prisms (0.82 g, 41%), m.p. 235-236° C.

Workup

  1. customprecipitating crystals
  2. filtrationwere collected by filtration
  3. washThe organic layer of the filtrate was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto give crude crystals
  7. customobtained previously
  8. customthis was followed by recrystallization from ethyl acetate - methanol

Sources & evidence

ORD record
ord-3ae554d6481c4bb7bff7dc0396bb5543
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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