2,4-Dimethoxybenzenesulfonyl chloride → HCID 23364241, compound

HRID 1081515Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=[O:16])[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=3)[C:4]=2[CH:3]=1.CC([O-])(C)C.[K+].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[S:35](Cl)(=[O:37])=[O:36]>C1COCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([S:35]([C:28]3[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:27]=3[O:26][CH3:25])(=[O:37])=[O:36])[C:7](=[O:16])[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 2 g of 5-chloro-3-(3-chlorophenyl)-1,3-dihydro-2H-benzimidazol-2-one in 170 ml of THF is cooled to -40° C. and 0.97 g of potassium tert- butylate is added. The mixture is stirred for 30 minutes at -10° C. and then cooled to -50° C. and a solution of 1.7 g of 2,4-dimethoxybenzenesulfonyl chloride in 70 ml of THF is added. The reaction mixture is stirred for 2 hours, the temperature being allowed to rise to RT, and then concentrated under vacuum. The residue is taken up with water, extracted with DCM and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 2.3 g of the expected product after crystallization from a cyclohexane/DCM mixture (90/10; v/v). M.p.=173° C.

Workup

temperaturecooled to -50° C.
stirringThe reaction mixture is stirred for 2 hours
customto rise to RT
concentrationconcentrated under vacuum
extractionextracted with DCM
dry with materialdried over Na2SO4
customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record: ord-593b216cd00943048be07625e8811c07
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585394

Reaction notes

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