Toluene → HCID 69861340, compound

HRID 362637Notes

Reaction equation

[OH-].[Na+].[C:3]1(C)[CH:8]=CC=[CH:5][CH:4]=1.[C:10]([N:14]1[CH:18]([NH2:19])[CH:17]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])[C:16](=[O:28])[NH:15]1)([CH3:13])([CH3:12])[CH3:11]>O>[C:10]([N:14]1[CH:18]([NH2:19])[CH:17]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])[C:16](=[O:28])[N:15]1[CH:3]([CH2:4][CH3:5])[CH3:8])([CH3:13])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To 160 mg of sodium hydroxide (60% oil dispersion) were added 30 ml of toluene and 1.00 g of 1-tert-butyl-4-(2,6-dichlorophenyl)-5-amino-pyrazolin-3-one, and the mixture was heated for 2 hours at 100° C. To this was added 550 ml of isopropyl mathanesulfonate, and the mixture was heated for additional 3 hours at 100° C. After completion of the reaction, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate anhydride, then, the solvent was distilled off under reduced pressure. The residue analyzed by 1H-NMR on the ratio of N-alkyl compound to O-alkyl compound being 31 to 69 was applied to column chromatography to obtain 353 mg (yield: 31%) of 1-tert-butyl-2-sec-butyl-4-(2,6-dichlorophenyl)-5-aminopyrazolin-3-one.

Workup

additionTo this was added 550 ml of isopropyl mathanesulfonate
temperaturethe mixture was heated for additional 3 hours at 100° C
additionwas added
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate anhydride
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-912a2e9dfdb748529b97494a61531dd8
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05869684

Reaction notes

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