Water → HCID 18945235, compound

HRID 399813Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].ClS([N:25]=[C:26]=O)(=O)=O.CN(C)C=O.O>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:17]=[CH:18][CH:19]=[C:20]2[C:26]#[N:25])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of methyl 3-acetoxymethyl-5-(pyrrol-1-yl)benzoate (4.68 g) in dichloromethane (94 ml) was added chlorosulfonyl isocyanate (2.1 ml) at -20° C. under nitrogen. After being stirred for 1 hour at -20° C., to the reaction mixture was added N,N-dimethylformamide (14.0 ml) at -20° C. After being stirred for 1 hour at -20° C. to -10° C., the reaction mixture was poured into water and the product was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to afford methyl 3-acetoxymethyl-5-(2-cyanopyrrol-1-yl)benzoate (4.26 g).

Workup

stirringAfter being stirred for 1 hour at -20° C. to -10° C.
extractionthe product was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated in vacuo
customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1)
additionThe eluted fractions containing the desired product
customwere collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-fdc9e6b942884a058ab4617c60010deb
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05824691

Reaction notes

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