Methanol → Methyl-7-sulfamoyl-1,4-benzodioxane-5-carboxylate

HRID 1659986Notes

Reaction equation

HRID 1659986 reaction equation
S(=O)(=O)(O)O.[S:6]([C:10]1[CH:11]=[C:12]([C:20]([OH:22])=[O:21])[C:13]2[O:18][CH2:17][CH2:16][O:15][C:14]=2[CH:19]=1)(=[O:9])(=[O:8])[NH2:7].[CH3:23]O>>[CH3:23][O:21][C:20]([C:12]1[C:13]2[O:18][CH2:17][CH2:16][O:15][C:14]=2[CH:19]=[C:10]([S:6](=[O:8])(=[O:9])[NH2:7])[CH:11]=1)=[O:22]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 205447607-Sulfamoyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

Product 1

HCID 20544687Methyl-7-sulfamoyl-1,4-benzodioxane-5-carboxylateYield 81.2%

Procedure

429 g of methanol were introduced into a balloon flask provided with a condenser and then, under cooling, 54 g of 93% sulfuric acid and 111 g of 7-sulfamoyl-1,4-benzodioxane-5-carboxylic acid were added. The mixture was heated under reflux and then cooled. The crystals were dried off, washed with methanol and then treated with 500 cm3 of water and 5 g of sodium carbonate. The precipitate was dried off, washed with water and dried. 95 g of methyl-7-sulfamoyl-1,4-benzodioxane-5-carboxylate were obtained (M.P.: 225°-226° C.; yield: 81%).

Workup

  1. customprovided with a condenser
  2. temperatureunder cooling
  3. temperatureThe mixture was heated
  4. temperatureunder reflux
  5. temperaturecooled
  6. customThe crystals were dried off
  7. washwashed with methanol
  8. additiontreated with 500 cm3 of water and 5 g of sodium carbonate
  9. customThe precipitate was dried off
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-286bc8a70d384ee4ae9b0e0d91929d81
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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