Phosphorus pentachloride → HCID 10448313, compound

HRID 1607675Notes

Reaction equation

HRID 1607675 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8](O)=[O:9].P(Cl)(Cl)(Cl)(Cl)[Cl:23]>C1C=CC=CC=1>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8]([Cl:23])=[O:9]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 10402218HCID 10402218, compound

Product 1

HCID 10448313HCID 10448313, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-(2,4-difluorophenoxy)-4-nitrobenzoic acid (1.5 g) and phosphorus pentachloride (1.1 g) in benzene (10 ml) was stirred for 1 hour at room temperature. The mixture was concentrated under reduced pressure to give crystals of 3-(2,4-difluorophenoxy)-4-nitrobenzoyl chloride. A solution of the above chloride in dichloromethane (5 ml) was added to a mixture of methoxylamine hydrochloride (0.85 g) and sodium bicarbonate (2.2 g) in water (10 ml) and dichloromethane (5 ml) at to 5° C. After stirring for 1 hour at the same temperature, the mixture was extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was crystallized from isopropyl ether to give pale brown crystals of N-methoxy-3-(2,4-difluorophenoxy)-4-nitrobenzamide (1.2 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-499ff7a9b0aa4e29a26cf1267556c958
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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