Diethylamine → 7-Diethylsulfamoyl-1,4-benzodioxane-5-carboxylic acid

HRID 1660021Notes

Reaction equation

HRID 1660021 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.Cl[S:14]([C:17]1[CH:18]=[C:19]([C:27]([OH:29])=[O:28])[C:20]2[O:25][CH2:24][CH2:23][O:22][C:21]=2[CH:26]=1)(=[O:16])=[O:15]>O>[CH2:1]([N:3]([CH2:4][CH3:5])[S:14]([C:17]1[CH:18]=[C:19]([C:27]([OH:29])=[O:28])[C:20]2[O:25][CH2:24][CH2:23][O:22][C:21]=2[CH:26]=1)(=[O:16])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 8471TriethylamineHCID 64553167-(Chlorosulphonyl)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid

Product 1

HCID 205447157-Diethylsulfamoyl-1,4-benzodioxane-5-carboxylic acidYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

200 ml of water, 100 ml of diethylamine and 200 ml of triethylamine were introduced into a balloon flask provided with an agitator and a thermometer and then 140 g of 7-chlorosulfonyl-1,4-benzodioxane-5-carboxylic acid were added in portions, the temperature being maintained at from 20°-30° C. The mixture was agitated at ambient temperature and then 500 ml of water were added. The solution was filtered and treated with 300 ml of hydrochloric acid. The precipitate was dried off, washed and dried. 117 g of 7-diethylsulfamoyl-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 149° C.; yield: 74%).

Workup

  1. customprovided with an agitator
  2. temperaturethe temperature being maintained at from 20°-30° C
  3. filtrationThe solution was filtered
  4. additiontreated with 300 ml of hydrochloric acid
  5. customThe precipitate was dried off
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-220b79ffa4f648e8bccfe32f8b720aa2
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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