Acetyl chloride → 3-Chloromethyl-1-(4-fluorophenyl)-pyrrolidine-2,5-dione

HRID 231559

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

In a variant of (b), into a toluene solution of 33.3 g (0.3 moles) 4-fluoroaniline, a toluene solution of 44.6 g (0.3 moles) 2-chloromethylsuccinic acid anhydride were added dropwise at room temperature while stirring. The temperature of the mixture rose to 40° C. during the operation. To the suspension of the semi-anilide obtained, 0.35 moles of acetylchloride was added dropwise at 60° C. while stirring, the addition being carried out so slowly that the ensuing gas development could be easily controlled. After 3 hours the reaction mixture was heated to 100° C. and held at that temperature until the gas development was terminated. The semi-anilide thereby dissolved. When the reaction mixture was cooled down, the desired product crystallized. The actual yield was 93% of the theoretical yield.

Workup

customrose to 40° C. during the operation
customobtained
stirringwhile stirring
additionthe addition
customwas terminated
dissolutionThe semi-anilide thereby dissolved
temperatureWhen the reaction mixture was cooled down
customthe desired product crystallized

Sources & evidence

ORD record: ord-384911e3274b45318b1e9fd76d82376d
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04847285

Linked notes

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