Chlorosulfonic acid → 5-[2-(3-Ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy benzenesulfonylchloride

HRID 2247330Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[C:10]([CH3:12])[N:11]=1)=[O:5])[CH3:2].[Cl:21][S:22](O)(=[O:24])=[O:23]>ClCCl>[CH2:1]([NH:3][C:4](=[O:5])[NH:6][C:7]1[S:8][C:9]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[C:17]([S:22]([Cl:21])(=[O:24])=[O:23])[CH:18]=2)=[C:10]([CH3:12])[N:11]=1)[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

A suspension of 1-ethyl-3-[5-(4-methoxy-phenyl)-4-methyl-thiazol-2-yl]urea (Example 28c) (1.0 g, 3.44 mmol) in dichloromethane (15 ml) is added portionwise to chlorosulfonic acid (25 ml, excess) cooled at −10° C. The temperature is kept below 0° C. throughout the addition. The reaction mixture is left to warm up to room temperature. After 3 hours, the reaction mixture is poured carefully onto ice (2 litres). Once ice is melted, the aqueous layer is extracted with dichloromethane (DCM) (3×200 ml). The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated to afford 5-[2-(3-ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy benzenesulfonylchloride.

Workup

additionThe temperature is kept below 0° C. throughout the addition
waitThe reaction mixture is left
temperatureto warm up to room temperature
additionthe reaction mixture is poured carefully onto ice (2 litres)
extractionthe aqueous layer is extracted with dichloromethane (DCM) (3×200 ml)
washThe combined organic layers are washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-314f409940aa418880a02f56519f96c9
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687637B2

Reaction notes

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