Chlorosulfonic acid → 5-(2-Acetylamino-4-methyl-thiazol-5-yl)-2-methoxy-benzenesulfonyl chloride
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=2[CH3:18])=[CH:5][CH:4]=1.[Cl:19][S:20](O)(=[O:22])=[O:21]>ClCCl>[C:15]([NH:14][C:12]1[S:13][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([S:20]([Cl:19])(=[O:22])=[O:21])[CH:7]=2)=[C:10]([CH3:18])[N:11]=1)(=[O:17])[CH3:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To N-[5-(4-Methoxy-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 28a) (0.0947 g, 0.361 mmol) is added at 0° C. chlorosulfonic acid (3 ml) followed by dichloromethane (1 ml). The reaction mixture is stirred below 0° C. for 2 hours then poured into crushed ice and extracted with dichloromethane (3×5 ml). The organic layers are combined and dried over MgSO4. The solvent is removed to give 5-(2-acetylamino-4-methyl-thiazol-5-yl)-2-methoxy-benzenesulfonyl chloride, which is dissolved into dioxane (2 ml). To this solution is added N,N-dimethyl-ethylenediamine (0.0636 g, 0.72 mmol) and 2M Na2CO3 (0.5 ml). The reaction mixture is stirred at room temperature for 2 hours. The mixture is concentrated and the residue is taken into water (2 ml) and extracted with dichloromethane (3×5 ml). The combined organic layers are dried over MgSO4. After filtration the solvent is removed in vacuo to give the titled compound which is dried overnight in vacuum oven at 25° C. MH+ (ESMS): Mp 413.0° C.
Workup
- additionthen poured
- custominto crushed ice
- extractionextracted with dichloromethane (3×5 ml)
- dry with materialdried over MgSO4
- customThe solvent is removed
Sources & evidence
- ORD record
- ord-930016136f1848339ccfde6899e0da0c
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687637B2
Reaction notes
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