4-Chlorobenzaldehyde → HCID 11550333, compound
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[N:3]1.[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[OH:13])=[CH:10][CH:9]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6.60 g of 1-methylpyrazole in 150 mL of tetrahydrofuran was cooled to −60° C., and 60 mL of a 1.6-M n-butyllithium/n-hexane solution was added dropwise to the solution under a nitrogen atmosphere. After the mixture was stirred for one hour, a solution of 11.288 g of 4-chlorobenzaldehyde in 50 mL of tetrahydrofuran was added dropwise to the mixture. It took 7 hours to bring back a temperature of the mixture to a room temperature, and then to the mixture, 125 mL of a 1-N ammonium chloride aqueous solution was added. The extraction with ethyl acetate was performed twice, and the extract was washed with a saturated saline solution. After the washed solution was dried over sodium sulfate, the solvent was distilled off. The raw product was purified by silica gel column chromatography (hexane/ethyl acetate (volume ratio)=1:2 to 1:3) to give the title compound (7.898 g (44%)).
Workup
- waitIt took 7 hours
- customto a room temperature
- extractionThe extraction with ethyl acetate
- washthe extract was washed with a saturated saline solution
- dry with materialAfter the washed solution was dried over sodium sulfate
- distillationthe solvent was distilled off
- customThe raw product was purified by silica gel column chromatography (hexane/ethyl acetate (volume ratio)=1:2 to 1:3)
Sources & evidence
- ORD record
- ord-af11810ac9bf4fd4881d17beb656fd7d
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365553B2
Reaction notes
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