Ammonium Chloride → HCID 69216303, compound

HRID 2221965Notes

Reaction equation

HRID 2221965 reaction equation
CC(C)([O-])C.[K+].C1(C)C=CC(S([CH2:16][N+:17]#[C-])(=O)=O)=CC=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:40]=[CH:41][C:42]=1[O:43][CH2:44][C:45]1[N:46]=[C:47]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:48][C:49]=1[CH3:50])[CH2:25][O:26][C:27]1[C:31]([CH:32]=O)=[CH:30][N:29]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:28]=1.[Cl-].[NH4+]>C(COC)OC.CO>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:40]=[CH:41][C:42]=1[O:43][CH2:44][C:45]1[N:46]=[C:47]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:48][C:49]=1[CH3:50])[CH2:25][O:26][C:27]1[C:31]([CH2:32][C:16]#[N:17])=[CH:30][N:29]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:28]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 86605805HCID 86605805, compound

Product 1

HCID 69216303HCID 69216303, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a mixture of potassium tert-butoxide (700 mg) and dimethoxyethane (10 mL) was added a solution of p-toluenesulfonylmethylisocyanide (650 mg) in dimethoxyethane (10 mL) at −78° C., and the mixture was stirred for 5 min. To the reaction mixture was added a solution of 3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-phenyl-1H-pyrazole-4-carbaldehyde (1.46 g) in dimethoxyethane (10 mL). After stirring at the same temperature for 1 hr, the mixture was stirred for 1 hr while warming to room temperature. To the reaction mixture was added methanol (20 mL), and the mixture was refluxed for 1 hr. After cooling, the reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give (3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-phenyl-1H-pyrazol-4-yl)acetonitrile (700 mg, yield 47%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, v/v). The crystals were recrystallized from ethyl acetate-hexane. melting point: 137-138° C.

Workup

  1. stirringAfter stirring at the same temperature for 1 hr
  2. stirringthe mixture was stirred for 1 hr
  3. temperaturethe mixture was refluxed for 1 hr
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e29d018fd1cf43edb96e814fe5b879ca
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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