Hydrochloric Acid → 2-Chloro-4'-isopropyl-3'-sulfamoylacetophenone

HRID 461160Notes

Reaction equation

HRID 461160 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][C:5]=1[S:13](=[O:16])(=[O:15])[NH2:14])([CH3:3])[CH3:2].[N+](=[CH2:19])=[N-].C(O)COCCO.COC.[ClH:30]>CCOCC>[Cl:30][CH2:19][C:8]([C:7]1[CH:11]=[CH:12][C:4]([CH:1]([CH3:3])[CH3:2])=[C:5]([S:13](=[O:16])(=[O:15])[NH2:14])[CH:6]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 212256572-(2-Hydroxyethoxy)ethanol;methoxymethaneHCID 227605054-Isopropyl-3-sulfamoylbenzoylchloride

Product 1

HCID 227606662-Chloro-4'-isopropyl-3'-sulfamoylacetophenone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

13.5 g of 4-isopropyl-3-sulfamoylbenzoyl chloride were reacted as prescribed in Example 66b) with diazomethane in ether, the 4'-isopropyl-3'-sulfamoyldiazoacetophenone remaining in solution without precipitating as crystals. The solution so obtained was allowed to flow into a mixture of 200 ml of diethylene glycol-dimethyl ether and 100 ml of concentrated hydrochloric acid while stirring and cooling with ice, whereafter the solvent was largely distilled off under reduced pressure. To the oily residue, 500 ml of water were added and the solution was extracted with 200 ml of ethyl acetate. Drying followed over sodium sulfate and the solvent was distilled off under reduced pressure. The oily residue crystallized in the course of 1 to 3 days and was then triturated under a small amount of xylene and filtered off. Melting point: 141° C.

Workup

  1. customthe 4'-isopropyl-3'-sulfamoyldiazoacetophenone remaining in solution without precipitating as crystals
  2. customThe solution so obtained
  3. temperaturecooling with ice, whereafter the solvent
  4. distillationwas largely distilled off under reduced pressure
  5. additionTo the oily residue, 500 ml of water were added
  6. extractionthe solution was extracted with 200 ml of ethyl acetate
  7. customDrying
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe oily residue crystallized in the course of 1 to 3 days
  10. customwas then triturated under a small amount of xylene
  11. filtrationfiltered off

Sources & evidence

ORD record
ord-37e224dcd70c4c6da65028c3c514d833
Source dataset
uspto-grants-1977_12
Patent number
US04061761

Reaction notes

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