Ethylene Glycol → HCID 20524789, compound

HRID 1105709Notes

Reaction equation

HRID 1105709 reaction equation
[O:1]=[C:2]([CH3:16])[CH2:3][N:4]([S:12]([CH3:15])(=[O:14])=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[OH-].[Na+].C1(C)C=CC=CC=1>[CH3:16][C:2]1([CH2:3][N:4]([S:12]([CH3:15])(=[O:14])=[O:13])[C:5]2[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=2)[O:19][CH2:18][CH2:17][O:1]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 20524745HCID 20524745, compound

Product 1

HCID 20524789HCID 20524789, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of N-(2-oxopropyl)-4'-chloromethanesulphonanilide (6.0 g), ethane-1,2-diol (10 ml), 4-toluenesulphonic acid (0.1 g) and toluene (75 ml) was stirred and boiled under reflux with water separation by means of a Dean and Stark receiver. After 3 hours the reaction mixture was cooled and poured into water (about 200 ml) containing a few drops of sodium hydroxide solution. The organic layer was separated, washed with water, dried (MgSO4) and evaporated to a brown oil, which gave fawn coloured crystals from a solution in toluene/80°-100° petrol. Yield 6.0 g (86%). Melting point 84°-85°.

Workup

  1. temperatureAfter 3 hours the reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated to a brown oil, which
  6. customgave

Sources & evidence

ORD record
ord-7e1570929e514708b5b8de24da4d9158
Source dataset
uspto-grants-1982_01
Patent number
US04309559

Reaction notes

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