Calcium Carbonate → 2,1,3-Benzothiadiazol-5-ylmethanol

HRID 1357749

Reaction equation

HRID 1357749 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]=1

Participants

4

Reactant 2

HCID 10112Calcium CarbonateHCID 5910045-(Bromomethyl)-2,1,3-benzothiadiazole

Product 1

HCID 27762942,1,3-Benzothiadiazol-5-ylmethanolYield 76.4%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

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

  1. customThe solvents were evaporated
  2. customthe residue was partitioned between 2N hydrochloric acid and methylene 6 3 chloride
  3. dry with materialThe organic layers were dried (magnesium sulfate)
  4. customevaporated
  5. 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

Linked notes

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