Phosgene → HCID 20537582, compound

HRID 1155674Notes

Reaction equation

Br.[NH2:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=2)[C:4]1=[O:17].[C:18](Cl)([Cl:20])=[O:19].C(N(CC)CC)C>C1(C)C=CC=CC=1.O1CCCC1>[Cl:20][C:18]([NH:2][CH:3]1[CH2:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([Cl:15])[CH:14]=2)[C:4]1=[O:17])=[O:19]

Participants

Conditions

Temperature: -33 °C

Procedure

After dilution with 200 ml of tetrahydrofurane, 34 g of 3-amino-1-(3,5-dichlorophenyl)pyrrolidine-2,5-dione hydrobromide (obtained in Example 2b) are added at -20° C. to 104 ml of a 20% solution of phosgene in toluene. Then 27.9 g of triethylamine in 100 ml of tetrahydrofurane are added dropwise at -37° to -28° C. and the reaction mixture is thereafter stirred for a further 12 hours at -33° C. to bring the reaction to completion. The precipitate is collected by filtration at -20° C. and the solution is concentrated. The 3-(N-chlorocarbonylamino)-1-(3,5-dichlorophenyl)pyrrolidine-2,5-dione obtained is used direct for the consequent reaction.

Workup

customthe reaction to completion
filtrationThe precipitate is collected by filtration at -20° C.
concentrationthe solution is concentrated

Sources & evidence

ORD record: ord-0a337038eb594658996fe7aabaa1c099
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04332816

Reaction notes

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