Ammonium Chloride → HCID 18957882, compound

HRID 2379126Notes

Reaction equation

HRID 2379126 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16](OC(C)C)=[O:17])=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[C:1]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:10]=3[N:9]=[CH:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18957903HCID 18957903, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18957882HCID 18957882, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1-(3-biphenylyl)-5-isopropoxycarbonylbenzimidazole (0.52 g, 1.6 mmol) in dry toluene (5 ml) under nitrogen at a temperature of -70° C. was added diisobutylaluminum hydride (1.1 ml of an 1.5M solution in toluene). After 1.5 h at -70° the reaction mixture was allowed to reach room temperature and was then poured in a slurry of 2M aqueous ammonium chloride and ice. After extractive workup with toluene the product was purified by chromatography on silica gel. Yield: 60 mg, 0.2 mmol, 12%. mp 130°-131° C.

Workup

  1. customto reach room temperature
  2. customAfter extractive workup with toluene the product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-83a81de1c465491f9ad135cc6f12c6cd
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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