Acrylonitrile → HCID 20310058, compound

HRID 2072023Notes

Reaction equation

[Cl:1][CH:2]([Cl:17])[C:3]([F:16])([F:15])[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[C:18](#[N:21])[CH:19]=[CH2:20].[ClH:22].C(N(CC)CC)C>C(#N)C>[Cl:22][CH:19]([CH2:20][S:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]([F:16])([F:15])[CH:2]([Cl:17])[Cl:1])=[CH:6][CH:7]=1)(=[O:13])=[O:12])[C:18]#[N:21]

Participants

Conditions

Temperature: 115 °C

Procedure

2-Chloro-3-((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)sulfonyl)propanenitrile (hereinafter "Compound") is prepared by mixing together 4-(2,2-dichloro-1,1-difluoroethoxy)benzenesulfonyl chloride with substantially two molecular proportions of acrylonitrile in the presence of acetonitrile, cupric chloride and triethylamine hydrochloride whereby the following reaction takes place: ##STR1## In the process, 4-(2,2-dichloro-1,1-difluoroethoxy)-benzenesulfonyl chloride (1 molar proportion), acrylonitrile (2 molar proportions), acetonitrile, anhydrous cupric chloride (.02 molar proportion) and triethylamine hydrochloride (0.032 molar proportion) are placed in a reaction vessel which is cooled, evacuated to about 2 mm mercury pressure, sealed and heated in an oil bath at about 115° C. for about six hours. The vessel is opened and the product is isolated by crystallization from methanol to give the title compound as a white, crystalline solid, melting at 109° C.

Workup

customthe following reaction
temperaturewhich is cooled
customevacuated to about 2 mm mercury pressure
customsealed
customthe product is isolated by crystallization from methanol

Sources & evidence

ORD record: ord-80440a01130d4b228f7543726247170a
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04049693

Reaction notes

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