Pyridine → HCID 19869783, compound
Reaction equation
[F:1][C:2]1[C:3]2[O:14][CH2:13][O:12][C:9]([C:10]=1[F:11])=[CH:8][C:4]=2[C:5](Cl)=[O:6].Cl.[CH3:16][O:17][NH:18][CH3:19].N1C=CC=CC=1>C(Cl)Cl>[CH3:19][N:18]([O:17][CH3:16])[C:5](=[O:6])[C:4]1[CH:8]=[C:9]2[O:12][CH2:13][O:14][C:3]=1[C:2]([F:1])=[C:10]2[F:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 14.4 grams (0.065 mole) of 3,4-difluoromethylenedioxybenzoyl chloride in 150 mL of methylene chloride was stirred and cooled to 0° C. To this was added 6.4 grams (0.066 mole) of O,N-dimethylhydroxylamine hydrochloride, followed by the dropwise addition of 11.0 mL (0.136 mole) of pyridine. Upon completion of addition the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was washed with two portions of aqueous 10% hydrochloric acid, two portions of aqueous IN sodium hydroxide, and two portions of an aqueous saturated solution of sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 15.1 grams of N-methyl-N-methoxy-3,4-difluoromethylenedioxybenzamide. The nmr spectrum was consistent with the proposed structure.
Workup
- additionUpon completion of addition the reaction mixture
- washThe reaction mixture was washed with two portions of aqueous 10% hydrochloric acid, two portions of aqueous IN sodium hydroxide, and two portions of an aqueous saturated solution of sodium chloride
- dry with materialThe organic layer was dried with sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1038ac0034da4f6cba31ee659c7a6ae8
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04895871
Reaction notes
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