Ammonium Chloride → HCID 178505397, compound

HRID 1875758Notes

Reaction equation

HRID 1875758 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[N:22]([CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:20]=3[N:19]=2)=[C:6]([CH:17]=1)[O:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13].[N-:36]=[N+:37]=[N-:38].[Na+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]2[N:22]([CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:20]=3[N:19]=2)=[C:6]([O:7][CH2:8][C:9]2[CH:16]=[CH:15][CH:14]=[C:11]([C:12]3[NH:38][N:37]=[N:36][N:13]=3)[CH:10]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67050025HCID 67050025, compound

Product 1

HCID 178505397HCID 178505397, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 3-[5-chloro-2-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-phenoxymethyl]-benzonitrile (0.15 g, 0.30 mmol) in N,N-dimethylformamide (10 ml) was added sodium azide (27 mg, 0.42 mmol) and ammonium chloride (22 mg, 0.42 mmol) and the reaction mixture was heated for 12 h at 120° C. The solvent was evaporated under reduced pressure, the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by column chromatography over silica gel (4-5% methanol/dichloromethane) to yield the desired compound as a colorless powder (14%). MS (Turbo Spray): m/z=535.2 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography over silica gel (4-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-9366b42c3aa94e79b11f020dddf4b27e
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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