Dimethylamine → 7-(N,N-dimethylsulphamoyl)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid

HRID 1413142Notes

Reaction equation

HRID 1413142 reaction equation
[CH3:1][NH:2][CH3:3].Cl[S:5]([C:8]1[CH:9]=[C:10]([C:18]([OH:20])=[O:19])[C:11]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[CH:17]=1)(=[O:7])=[O:6]>CC(C)=O>[CH3:1][N:2]([CH3:3])[S:5]([C:8]1[CH:9]=[C:10]([C:18]([OH:20])=[O:19])[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 674DimethylamineHCID 64553167-(Chlorosulphonyl)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid

Product 1

HCID 64553187-(N,N-dimethylsulphamoyl)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

500 cm3 of acetone and a solution of 99 g of dimethylamine in 250 cm3 of acetone were introduced into a balloon flask provided with an agitator and a thermometer. The mixture was cooled to 0° C. and then 139 g of 7-chlorosulfonyl-1,4-benzodioxane-5-carboxylic acid were introduced. The mixture was agitated at ambient temperature, the acetone distilled off and the residue dissolved in 1 liter of water. The solution was rendered alkaline, filtered and treated with 70 cm3 of hydrochloric acid. The precipitate was dried off, washed and dried. 128 g of 7-dimethylsulfamoyl-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 220°-221° C.; yield: 89%).

Workup

  1. customprovided with an agitator
  2. distillationthe acetone distilled off
  3. dissolutionthe residue dissolved in 1 liter of water
  4. filtrationfiltered
  5. additiontreated with 70 cm3 of hydrochloric acid
  6. customThe precipitate was dried off
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-7eb611f40f8248f98e057913e4db0557
Source dataset
uspto-grants-1981_02
Patent number
US04248885

Reaction notes

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