Ammonia → HCID 178439618, compound
Reaction equation
Cl[C:2](Cl)([CH:5]([CH3:7])C)[CH:3]=O.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH3:17].[C:18](#[N:20])C>>[C:10]1([C:9]2[NH:20][CH:18]=[C:3]([CH2:2][CH2:5][CH3:7])[N:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
Procedure
A mixture consisting of 1.55 g of 2,2-dichloroisovaleraldehyde, 1.27 g of benzaldehyde, and 8 ml of acetonitrile was cooled in an ice-water, and to the mixture was added 13.5 ml of concentrated aqueous ammonia, and then the resulting mixture was stirred for 66 hours at room temperature. The product was extracted with methylene chloride, and the extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated to yield a crude product. The crude product was chromatographed using 30 g of silica gels, thereby contaminants which were eluted with 5% acetonitrile/methylene chloride were removed, and fractions which were eluted with 50% acetonitrile/methylene chloride were collected. The collected fractions were evaporated to yield 1.24 g of the residue, which was recrystallized from methylene chloride/ether to yield 0.947 g of crystals (yield: 51%).
Workup
- extractionThe product was extracted with methylene chloride
- washthe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- customto yield a crude product
- customThe crude product was chromatographed
- washcontaminants which were eluted with 5% acetonitrile/methylene chloride
- customwere removed
- washfractions which were eluted with 50% acetonitrile/methylene chloride
- customwere collected
- customThe collected fractions were evaporated
Sources & evidence
- ORD record
- ord-93ca63d9936848f29b51c66b1f30b8ae
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05312927
Reaction notes
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