Hydrochloric Acid → Methanesulfonamide, N-[4-(2-chloroacetyl)phenyl]-

HRID 65238

Reaction equation

HRID 65238 reaction equation
[C:1]1([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][CH2:13][C:14](Cl)=[O:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:12][CH2:13][C:14]([C:4]1[CH:3]=[CH:2][C:1]([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 70970Methanesulfonamide, N-phenyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 116629Methanesulfonamide, N-[4-(2-chloroacetyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

In a flask containing 128.4 g (0.75 mole) of N-phenylmethanesulfonamide, 169.5 g (1.50 mole) of chloroacetyl chloride in 1 L of methylene chloride under an atmosphere of nitrogen and cooled to about -10° C. add 300 g (2.25 mole) of aluminum chloride. Stir the resulting mixture for about 2 hours at -10° C. then warm to room temperature for about 16 hours. Pour the reaction mixture onto 2 Kg of ice containing 600 mL of concentrated hydrochloric acid. Collect the precipitate and wash with methanol (3×300 mL) and dry in vacuo to give the title compound.

Workup

  1. temperaturethen warm to room temperature for about 16 hours
  2. customCollect the precipitate
  3. washwash with methanol (3×300 mL)
  4. customdry in vacuo

Sources & evidence

ORD record
ord-b24a3c0eee3e49658076d6d493e15730
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Linked notes

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