Hydrochloric Acid → 3,4-Dichloro-N-methylbenzene-1-sulfonamide

HRID 1642120Notes

Reaction equation

HRID 1642120 reaction equation
Cl.CN.C[CH2:5][N:6](CC)CC.[Cl:11][C:12]1[CH:13]=[C:14]([S:19](Cl)(=[O:21])=[O:20])[CH:15]=[CH:16][C:17]=1[Cl:18].Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([S:19]([NH:6][CH3:5])(=[O:21])=[O:20])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 8471TriethylamineHCID 6364545Methylamine hydrochloride

Product 1

HCID 2229183,4-Dichloro-N-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methylamine hydrochloride (5.5 g, 81.46 mmol) was dissolved in DCM (300 ml), and Et3N (40 ml, 285.11 mmol) was added thereto. The reaction solution was then cooled to 0° C.; 3,4-dichlorobenzenesulfonyl chloride (20.00 g, 81.46 mmol) dissolved in DCM (50 ml) was then added dropwise, and stirring was carried out overnight at room temperature (TLC monitoring, silica gel, ethyl acetate). When the reaction was complete, 0.5 N HCl was added, the phases were separated, and the organic phase was washed with water and dried (sodium sulfate). The solvent was removed using a rotary evaporator. Purification was carried out by column chromatography on silica gel (gradient heptane/ethyl acetate 4:1 to 2:1).

Workup

  1. additionwas then added dropwise
  2. customthe phases were separated
  3. washthe organic phase was washed with water
  4. dry with materialdried (sodium sulfate)
  5. customThe solvent was removed
  6. customa rotary evaporator
  7. customPurification

Sources & evidence

ORD record
ord-a58684e9d3334de1882d1067e98e929d
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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