Hydrochloric Acid → HCID 855936, compound
Reaction equation
Cl[C:2](=[N:9][N:10]=[C:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>CN(C)C1C=CC=CC=1>[CH3:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:9][N:10]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
Then, 5.1 g (17.6 mmol) of [chloro(2-methylphenyl)methanone][chloro(phenyl)methylidene]hydrazone obtained in Step 2, 60 ml of dimethylaniline, and 4.9 g (52.8 mmol) of aniline were put into a 500-ml recovery flask and heated and stirred at 120° C. for 7 hours. After the stirring, the reacted solution was added to 1N hydrochloric acid and the mixture was stirred for 30 minutes. Then, an organic layer was extracted with dichloromethane. This organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine. Purification by column chromatography was then performed. A mixed solvent of toluene and ethyl acetate in a ratio of 1:1 was used as a developing solvent. The obtained fraction was concentrated to give 3.4 g of a white solid of Hmpptz in a yield of 63%. A synthesis scheme of Step 3 is shown in (a-3).
Workup
- temperatureheated
- stirringthe mixture was stirred for 30 minutes
- extractionThen, an organic layer was extracted with dichloromethane
- washThis organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine
- customPurification by column chromatography
- concentrationThe obtained fraction was concentrated
Sources & evidence
- ORD record
- ord-156f8537a9b0488b917694e77ec75386
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309458B2
Reaction notes
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