Water → HCID 13850776, compound

HRID 1382206Notes

Reaction equation

HRID 1382206 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][N:11]([CH2:15][CH2:16][OH:17])[CH2:12][CH2:13][OH:14])([O-:3])=[O:2].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.[OH2:29]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][N:11]([CH2:15][CH2:16][O:17][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:25])=[O:29])[CH2:12][CH2:13][O:14][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 13850775HCID 13850775, compound

Product 1

HCID 13850776HCID 13850776, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

389 g (1.5 mol) of crude N-(2-nitrophenylsulphenyl)-bis(2-hydroxyethyl)-amine are dissolved in 2 l of absolute pyridine, and 580 g (3 mol) of 4-toluenesulphonyl chloride are added at -10° in the course of 20 minutes. The mixture is stirred at -5° to 0° for 4 hours and left to stand at 0° overnight, and 4 l of water are added. Thereafter, the mixture is extracted with 3×1 l of methylene chloride and the extract is washed with 7×1 l of water, dried with sodium sulphate and concentrated. The oily residue is stirred with 1 l of a mixture of acetonitrile/methanol (1:1), a solid product precipitating, which is filtered off with suction with methanol. Yield: 423.6 g of melting point 91°-93°.

Workup

  1. waitleft
  2. waitto stand at 0° overnight
  3. extractionThereafter, the mixture is extracted with 3×1 l of methylene chloride
  4. washthe extract is washed with 7×1 l of water
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. stirringThe oily residue is stirred with 1 l of a mixture of acetonitrile/methanol (1:1)
  8. customa solid product precipitating
  9. filtrationwhich is filtered off with suction with methanol

Sources & evidence

ORD record
ord-aed78bf9dd964d82996027db4dccf9c2
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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