Trimethyl orthoformate → HCID 70152849, compound
Reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](=[N:21][OH:22])[NH2:20])[C:3]=1[S:23][CH3:24].O.[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:37](OC)(OC)[O:38][CH3:39]>>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([N:1]=[CH:37][O:38][CH3:39])=[C:3]([S:23][CH3:24])[C:4]([C:19]2[N:20]=[CH:26][O:22][N:21]=2)=[N:5]1Participants
4
Procedure
5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthio-3-pyrazolecarboxamide oxime (1.77 g, 4.4 mmol) was dissolved in 25 ml of trimethyl orthoformate, and then p-toluenesulfonic acid monohydrate (130 mg) was added at room temperature. The mixture was heated. under reflux for 2 hours. The trimethyl orthoformate was distilled off under reduced pressure and the residue was dissolved in 60 ml of ethyl acetate. After the solution was washed with 120 ml of an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, the solvent was distilled off to obtain a yellow crystal which was washed with n-hexane to yield 1.47 g (3.3 mmol) of the title compound as a pale yellow crystal. Yield 74%.
Workup
- temperatureThe mixture was heated
- temperatureunder reflux for 2 hours
- distillationThe trimethyl orthoformate was distilled off under reduced pressure
- dissolutionthe residue was dissolved in 60 ml of ethyl acetate
- washAfter the solution was washed with 120 ml of an aqueous saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off
- customto obtain a yellow crystal which
- washwas washed with n-hexane
Sources & evidence
- ORD record
- ord-83a8f723d38941b295793d1cc0277773
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06316477B1
Reaction notes
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