Ammonium Chloride → HCID 69425928, compound

HRID 1295271Notes

Reaction equation

HRID 1295271 reaction equation
CC(C)([O-])C.[K+].C1(C)C=CC(S([CH2:16][N+:17]#[C-])(=O)=O)=CC=1.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[O:26][C:27]([CH3:55])=[C:28]([CH2:30][O:31][C:32]2[CH:52]=[CH:51][C:35]([CH2:36][O:37][C:38]3[CH:42]=[C:41]([CH:43]=O)[N:40]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:39]=3)=[CH:34][C:33]=2[O:53][CH3:54])[N:29]=1.[Cl-].[NH4+]>C(COC)OC.CO>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[O:26][C:27]([CH3:55])=[C:28]([CH2:30][O:31][C:32]2[CH:52]=[CH:51][C:35]([CH2:36][O:37][C:38]3[CH:42]=[C:41]([CH2:43][C:16]#[N:17])[N:40]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:39]=3)=[CH:34][C:33]=2[O:53][CH3:54])[N:29]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 865916713-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazole-5-carbaldehyde

Product 1

HCID 69425928HCID 69425928, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a mixture of potassium t-butoxide (1.46 g) and dimethoxyethane (50 ml) was added a solution of p-toluenesulfonylmethyl isocyanide (1.33 g) in dimethoxyethane (50 ml) at −78° C. and the mixture was stirred for 5 min. Then a solution of 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazole-5-carbaldehyde (3.00 g) in dimethoxyethane (50 ml) was added. After stirring at said temperature for 1 hr, the mixture was stirred for 1 hr. while raising the temperature to room temperature. To the obtained mixture was added methanol (50 ml), and the mixture was refluxed for 2 hrs. After cooling, the reaction solution 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 (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and [3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy-]-1-phenyl-1H-pyrazol-5-yl]acetonitrile (450 mg, yield 15%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 141–142° C.

Workup

  1. stirringAfter stirring
  2. customfor 1 hr
  3. stirringthe mixture was stirred for 1 hr
  4. temperaturethe mixture was refluxed for 2 hrs
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-794f49b6492747df811d0d2fb0fdb0e8
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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