Thionyl Chloride → 7-Nitro-1,4-benzodioxane-5-carbonyl chloride

HRID 127448Notes

Reaction equation

HRID 127448 reaction equation
S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:9]=[C:10]([C:18]([OH:20])=O)[C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=1)([O-:7])=[O:6]>CN(C)C=O>[N+:5]([C:8]1[CH:9]=[C:10]([C:18]([Cl:3])=[O:20])[C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=1)([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 124645337-Nitro-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

Product 1

HCID 205447457-Nitro-1,4-benzodioxane-5-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

112 ml of thionyl chloride, 56 g of 7-nitro-1,4-benzodioxane-5-carboxylic acid were introduced into a 250 ml balloon flask provided with a stirrer, a thermometer and a reflux condenser. The mixture was stirred and 1 ml of dimethylformamide was added with heating. After stirring for one hour at the reflux temperature, the excess of thionyl chloride was removed by distillation under vacuum. 61 g of 7-nitro-1,4-benzodioxane-5-carbonyl chloride were obtained (M.P.: 108° C.; yield: 100%).

Workup

  1. customprovided with a stirrer
  2. temperaturewith heating
  3. stirringAfter stirring for one hour at the reflux temperature
  4. customthe excess of thionyl chloride was removed by distillation under vacuum

Sources & evidence

ORD record
ord-13d36516524b43fa94487556b6178ebb
Source dataset
uspto-grants-1981_03
Patent number
US04255580

Reaction notes

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