5-Isopropyl-1,3,4-thiadiazol-2-amine → Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester
Reaction equation
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH:15]([C:18]1[S:22][C:21]([NH2:23])=[N:20][N:19]=1)([CH3:17])[CH3:16]>N1C=CC=CC=1>[CH:15]([C:18]1[S:22][C:21]([NH:23][S:2]([C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=2)(=[O:4])=[O:3])=[N:20][N:19]=1)([CH3:17])[CH3:16]Participants
Procedure
4.1 g acetic acid 4-chlorosulfonyl-phenyl ester were added to a stirred solution of 2.5 g 5-isopropyl-[1,3,4]thiadiazol-2-ylamine in 35 ml pyridine. The reaction mixture was stirred at room temperature overnight. The pyridine was removed in vacuo and the residue dissolved in 200 ml dichloromethane and washed with 60 ml water. The organic layer was dried over MgSO4. Then the solvent was removed in vacuo and the resulting residue purified by flash chromatography on silica gel with the eluents n-heptane:ethyl acetate=1:1=>1:3 to obtain 4.47 g Acetic acid 4-(5-isopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl ester impurified with 40% of the byproduct N-(5-Isopropyl-[1,3,4]thiadiazol-2-yl)-acetamide. The material was used without further purification.
Workup
- customThe pyridine was removed in vacuo
- dissolutionthe residue dissolved in 200 ml dichloromethane
- washwashed with 60 ml water
- dry with materialThe organic layer was dried over MgSO4
- customThen the solvent was removed in vacuo
- customthe resulting residue purified by flash chromatography on silica gel with the eluents n-heptane
Sources & evidence
- ORD record
- ord-8dd9fb98e8ba41b18ab82ddcaa4910b0
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910612B2
Reaction notes
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