Sulfuric Acid → Dichloro-1,2-thiazole-4-carboxylic acid
Reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]1[S:10][N:9]=[C:8]([Cl:11])[C:7]=1[C:12](N)=[O:13].S(=O)(=O)(O)[OH:16]>O>[Cl:5][C:6]1[S:10][N:9]=[C:8]([Cl:11])[C:7]=1[C:12]([OH:13])=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
NaNO2 (1 g, 14.49 mmol, 1.13 equiv), water (30 ml), dichloro-1,2-thiazole-4-carboxamide (2 g, 10.15 mmol, 1.00 equiv) was added to the sulfuric acid solution of the 3,5-dichloroisothiazole-4-carboxamide. The resulting solution was stirred for 30 min at 50° C. The resulting solution was extracted with 3×30 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated. This resulted in 400 mg (crude) of dichloro-1,2-thiazole-4-carboxylic acid as a brown solid.
Workup
- extractionThe resulting solution was extracted with 3×30 mL of dichloromethane
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThis resulted in 400 mg (crude) of dichloro-1,2-thiazole-4-carboxylic acid as a brown solid
Sources & evidence
- ORD record
- ord-b4db5afc90e24167ae1bf25f895a9075
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067898B1
Reaction notes
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