Diethanolamine → 4-Amino-N,N-bis(2-hydroxyethyl)benzenesulfonamide

HRID 861188Notes

Reaction equation

HRID 861188 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][OH:10].C([C:17]1[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][C:18]=1[S:19](Cl)(=[O:21])=[O:20])(=O)C>O>[OH:10][CH2:9][CH2:8][N:7]([CH2:11][CH2:12][OH:13])[S:19](=[O:21])([C:18]1[CH:23]=[CH:24][C:25]([NH2:27])=[CH:26][CH:17]=1)=[O:20]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 10340Sodium CarbonateHCID 18792301Acetylsulfanilylchlorid2×

Product 1

HCID 2562924-Amino-N,N-bis(2-hydroxyethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N1,N1 -bis(2-hydroxyethyl) sulfanilamide was prepared as follows. (This method was taken in part from G. DiModica and E. Angeletti, Gazz. chim. ital., 1960, 90, 434-9 [CA 55:11344d].) A mixture of sodium carbonate (55.6 g), D.I. water (120 mL), and diethanolamine (57.8 g) was stirred and heated to 60°-70° C. Acetylsulfanilyl chloride (116.8 g) was added as a solid over an hour. D.I. water (225 mL) was added in portions during the acetylsulfanilyl chloride addition to keep the mixture stirrable. The mixture was stirred for an additional 3 hours at 60°-70° C., then allowed to cool to room temperature for about 16 hours. The solids were isolated by filtration and washed with 200 mL cold D.I. water.

Workup

  1. temperatureheated to 60°-70° C
  2. customThe solids were isolated by filtration
  3. washwashed with 200 mL cold D.I

Sources & evidence

ORD record
ord-b07a9f0eaf524cf384265045e6a0ea0b
Source dataset
uspto-grants-1998_02
Patent number
US05713988

Reaction notes

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