4-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride → HCID 59483781, compound

HRID 1808372Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10](Cl)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1.Cl.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=2)[CH2:18][CH2:17]1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=3)[CH2:18][CH2:17]2)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride (1.3 g, 0.0056 mol) was added at 25° C., under argon, to a solution of methyl indoline-6-carboxylate hydrochloride (1.2 g, 0.0056 mol) in dry pyridine (12 ml), and the resulting reaction mixture was stirred overnight at 70° C. The solvent was removed in vacuo, and the residue was taken up in dichloromethane and washed with water (2×), saturated copper sulfate solution (2×) and saturated sodium chloride solution, then dried (Na2SO4) and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 10-30% ethyl acetate in hexane). Yield: 1.9 g (90%)

Workup

customthe resulting reaction mixture
customThe solvent was removed in vacuo
washwashed with water (2×), saturated copper sulfate solution (2×) and saturated sodium chloride solution
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting crude product was purified by column chromatography (silica gel, 10-30% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-c89a20c912424c5aaac407b55f990aca
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357717B2

Reaction notes

Loading…