Sodium hydride → HCID 54499506, compound

HRID 1940503Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[NH:12][C:11]2=[O:21])=[CH:6][C:5]=1[CH:22]=[N:23][O:24][CH3:25].[N+:26](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>CN(C)C=O>[NH2:26][N:12]1[C:13]([C:17]([F:18])([F:19])[F:20])=[CH:14][C:15](=[O:16])[N:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[C:5]([CH:22]=[N:23][O:24][CH3:25])[CH:6]=2)[C:11]1=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

0.38 g (16 mmol) of sodium hydride in 50 ml of anhydrous dimethylformamide was treated dropwise at 0°-5° C. with a solution of 5.0 g (14 mmol) of 3-(4-chloro-3-methoxyiminomethylphenyl)-2,4-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 50 ml of anhydrous dimethylformamide. A solution of 2.8 g (14 mmol) of 2,4-dinitrophenoxyamine in 50 ml of anhydrous dimethylformamide was added dropwise to this mixture after 10 minutes, after which it was stirred for 60 hours at 20°-25° C. and for 6 hours at 50° C. For working up, the cooled reaction mixture was poured into 800 ml of ice water. The aqueous phase was extracted three times with 200 ml of ethyl acetate each time. The ethyl acetate extracts were then dried over sodium sulfate and concentrated. After chromatographic purification of the crude product on silica gel (eluent: cyclohexane/ethyl acetate/triethylamine 79:20:1), 1.5 g (29%) of a colorless oil were obtained.

Workup

customthe cooled reaction mixture
extractionThe aqueous phase was extracted three times with 200 ml of ethyl acetate each time
dry with materialThe ethyl acetate extracts were then dried over sodium sulfate
concentrationconcentrated
customAfter chromatographic purification of the crude product on silica gel (eluent: cyclohexane/ethyl acetate/triethylamine 79:20:1)

Sources & evidence

ORD record: ord-62eb9de115344c2eb892d1d76d4f1322
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05700805

Reaction notes

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