Triethylamine → alpha-(4-Methacryloxybenzenesulfonyloxyimino)thien-2-ylacetonitrile

HRID 648771Notes

Reaction equation

C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:18][N:19]=[C:20]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[C:21]#[N:22])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:28]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:18][N:19]=[C:20]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[C:21]#[N:22])(=[O:17])=[O:16])=[CH:11][CH:10]=1)(=[O:32])[C:29]([CH3:31])=[CH2:30]

Participants

Conditions

Temperature: 0 °C

Procedure

2.2 g (0.022 mole) of triethylamine and 0.5 g of 4-dimethylaminopyridine are added to a solution of 6.1 g (0.022 mole) of α-(4-hydroxybenzenesulfonyloxyimino)thien-2-ylacetonitrile (3a) in 75 ml of methylene chloride. With cooling to 0° C., a solution of 2.3 g (0.022 mole) of methacryloyl chloride in 20 ml of CH2Cl2 is added dropwise, and the reaction mixture is stirred for 3 hours at 0° C. The mixture is then filtered through silica gel, the filtrate is concentrated by evaporation, and the residue is recrystallised from methylene chloride/hexane, affording 5.92 g of the title compound with a melting point of 165°-166° C.

Workup

filtrationThe mixture is then filtered through silica gel
concentrationthe filtrate is concentrated by evaporation
customthe residue is recrystallised from methylene chloride/hexane

Sources & evidence

ORD record: ord-cb43066d5a90454c9dd27bcc57d8318e
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04736055

Reaction notes

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