Dimethylformamide → HCID 13518303, compound

HRID 1704392Notes

Reaction equation

HRID 1704392 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([S:14]([OH:17])(=O)=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][S:10]([CH3:13])(=[O:12])=[O:11].CN(C)C=O.P(Cl)(Cl)([Cl:25])=O>O.C1C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]([S:14]([Cl:25])(=[O:17])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][S:10]([CH3:13])(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 5360545SodiumHCID 14317957HCID 14317957, compound

Product 1

HCID 13518303HCID 13518303, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Sodium salt of 3-chloro-4-methylsulfonyloxybenzene sulfonic acid (453 g: 1.47 moles), N,N-dimethylformamide (21.1 g: 0.288 mole) and benzene (2000 cc) were mixed and heated with stirring until the mixture was refluxed. Phosphorus oxychloride (237 g: 1.55 moles) was added dropwise to the mixture for 1 hour. The resultant mixture was refluxed with stirring for an additional 3 hours and then water (1000 cc) was added to the resultant mixture under the temperature 20° C.-30° C. with cooling. The mixture was stirred for 1 hour under the same temperature and then the layer of benzene was separated from the mixture. The benzene solution separated was washed with water two times and dried over anhydrous sodium sulfate. Benzene was removed from the benzene solution by distillation to obtain crude white crystals (335. g) of 3-chloro-4-methylsulfonyloxybenzene sulfonylchloride. The crude white crystals were recrystalized from benzene. Yield: 74.7%. Melting point: 100°-100.5° C.

Workup

  1. temperatureheated
  2. temperaturewas refluxed
  3. stirringwith stirring for an additional 3 hours
  4. temperaturewith cooling
  5. stirringThe mixture was stirred for 1 hour under the same temperature
  6. customthe layer of benzene was separated from the mixture
  7. customThe benzene solution separated
  8. washwas washed with water two times
  9. dry with materialdried over anhydrous sodium sulfate
  10. customBenzene was removed from the benzene solution by distillation

Sources & evidence

ORD record
ord-932af53168884b318ad0267b2277f0f1
Source dataset
uspto-grants-1978_11
Patent number
US04126696

Reaction notes

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