Calcium Carbonate → 2,1,3-Benzothiadiazol-5-ylmethanol
Reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2=[N:7][S:8][N:9]=[C:5]2[CH:4]=1.C(=O)([O-])[O-:13].[Ca+2]>O1CCOCC1.O>[OH:13][CH2:2][C:3]1[CH:11]=[CH:10][C:6]2=[N:7][S:8][N:9]=[C:5]2[CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Bromomethylbenzo-2,1,3-thiadiazole (4.8 g) and calcium carbonate (10 g) were heated at reflux in 1:1 dioxane/water (120 mL) for 3 hours. The solvents were evaporated and the residue was partitioned between 2N hydrochloric acid and methylene 6 3 chloride. The organic layers were dried (magnesium sulfate), evaporated and chromatographed on silica gel eluting with 1:1 ethyl acetate/hexane to provide 2.66 g of the title compound.
Workup
- customThe solvents were evaporated
- customthe residue was partitioned between 2N hydrochloric acid and methylene 6 3 chloride
- dry with materialThe organic layers were dried (magnesium sulfate)
- customevaporated
- customchromatographed on silica gel eluting with 1:1 ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-029bc9b646b04e428b99707522c2021c
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06593335B1
Reaction notes
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