Hydrochloric Acid → HCID 178526584, compound

HRID 486002Notes

Reaction equation

HRID 486002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH:15]([CH2:19][CH2:20][OH:21])[CH2:16][CH2:17][OH:18].Cl>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[OH:18][CH2:17][CH2:16][N:15]([CH2:19][CH2:20][OH:21])[SH:8](=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8113Diethanolamine

Product 1

HCID 178526584HCID 178526584, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-chloro-3-nitrobenzene sulphonyl chloride (157.65 g; 0.616 mol) in acetone A.R. (300 ml), diethanolamine (155.19 g; 1.478 mol) was added dropwise at <20° C. over 1 hour. After stirring for a further 11/2 hours at <20° C. the yellow/brown reaction mixture was poured into ice/water (1500 g) with stirring. The resulting mixture was stirred for 11/2 hours and then the pH adjusted to pH7 by the addition of concentrated hydrochloric acid SG 1.18, filtered and washed copiously with water (3 liter). The residue was dried (40° C. vac oven) to give a pale yellow solid (156.89 g; 78% m.pt.96°)

Workup

  1. stirringwith stirring
  2. stirringThe resulting mixture was stirred for 11/2 hours
  3. filtrationfiltered
  4. washwashed copiously with water (3 liter)
  5. customThe residue was dried (40° C. vac oven)
  6. customto give a pale yellow solid (156.89 g; 78% m.pt.96°)

Sources & evidence

ORD record
ord-3c7e58fc7639445997298208ee23c5de
Source dataset
uspto-grants-1994_03
Patent number
US05290630

Reaction notes

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