Chlorine → N-(3-Chloro-2,6-dimethylphenyl)-2-methoxy-N-(2-oxooxolan-3-yl)acetamide

HRID 2414136Notes

Reaction equation

[Cl:1]Cl.[CH3:3][O:4][CH2:5][C:6]([N:8]([CH:17]1[CH2:21][CH2:20][O:19][C:18]1=[O:22])[C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16])=[O:7]>C(O)=O.[Fe](Cl)(Cl)Cl>[CH3:3][O:4][CH2:5][C:6]([N:8]([CH:17]1[CH2:21][CH2:20][O:19][C:18]1=[O:22])[C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([Cl:1])[C:10]=1[CH3:16])=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

Over 2 hours, 74.6 g (1.05 moles) of chlorine are introduced at 25°-30° C. into a solution of 277 g (1.0 mole) of N-methoxyacetyl-N-(2-oxotetrahydro-3-furyl)-2,6-dimethylaniline and 5 g of iron(III) chloride in 300 ml of 85% formic acid. The reaction is exothermic and virtually no gas evolves. When the addition of chlorine is complete, the reaction mixture is stirred for 30 minutes at 25° C., the formic acid is then distilled off in vacuo, the residue is taken up in 500 ml of toluene and the toluenic solution is washed with 100 ml of water. The oily residue obtained after the toluene has been distilled off is crystallised from a mixture of isopropanol and hexane, affording 287 g (92% of theory) of N-methoxyacetyl-N-(2-oxotetrahydro-3-furyl)-3-chloro-2,6-dimethylaniline with a melting point of 80°-82° C.

Workup

distillationthe formic acid is then distilled off in vacuo
washthe toluenic solution is washed with 100 ml of water
customThe oily residue obtained after the toluene
distillationhas been distilled off
customis crystallised from a mixture of isopropanol and hexane

Sources & evidence

ORD record: ord-507652bfd56a4cb38292e04a74e21e9b
Source dataset: uspto-grants-1988_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04721797

Reaction notes

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