Sodium Hydroxide → N-(2-Chloro-3-pyridinyl)-4-(methylamino)-N,1,3-trimethyl-1H-pyrazole-5-carboxamide
Reaction equation
[Cl:1][C:2]1[C:7]([N:8]([CH3:30])[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([CH3:17])[C:12]=2[NH:18][CH2:19]S(C2C=CC(C)=CC=2)(=O)=O)=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>>[Cl:1][C:2]1[C:7]([N:8]([CH3:30])[C:9]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([CH3:17])[C:12]=2[NH:18][CH3:19])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1Participants
Procedure
A mixture of 40.8 gm (0.091 mol) of N-(2-chloro-3-pyridinyl)-4-[[(4-methylphenyl)-sulfonyl]methylamino]-N,1,3-trimethyl-1H-pyrazole-5-carboxamide (prepared from N-(2-chloro-3-pyridinyl)-4-[[(4-methylphenyl)-sulfonyl]amino]-N,1,3-trimethyl-1H-pyrazole-5-carboxamide by reaction with sodium hydride in anhydrous N,N-dimethylformamide and subsequent reaction with methyl iodide) and 0.6 kg of polyphosphoric acid (content of phosphorpentoxide: 85%) was heated with stirring for 6 hours up to 60° C. The warm reaction mixture was stirred into cracked ice and subsequently mixed by means of external cooling with ice water with 40% aqueous sodium hydroxide solution until the precipitation was finished. After standing for 2 hours at +5° C., the strongly acidic reaction mixture was filtered off by suction filtration. The filtration residue was carefully washed with water and subsequently dried in the air. Yield: 20.9 gm (78% of theory).
Workup
- temperaturewas heated
- customThe warm reaction mixture
- stirringwas stirred into cracked ice
- additionsubsequently mixed by means
- filtrationthe strongly acidic reaction mixture was filtered off by suction filtration
- washThe filtration residue was carefully washed with water
- customsubsequently dried in the air
Sources & evidence
- ORD record
- ord-f4f713a5b2054b6aaf629ff7d559a0ce
- Source dataset
- uspto-grants-1983_04
- Patent number
- US04381303
Reaction notes
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