Methylamine → N-methyl-4-(4-chlorophenoxy)benzene-sulfonamide

HRID 2300256Notes

Reaction equation

HRID 2300256 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1>O1CCCC1.C(Cl)Cl>[CH3:1][NH:2][S:17]([C:14]1[CH:15]=[CH:16][C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 27577504-(4-Chlorophenoxy)benzene-1-sulfonyl chloride

Product 1

HCID 18549775N-methyl-4-(4-chlorophenoxy)benzene-sulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 20 ml of a 2 molar solution of methylamine in tetrahydrofuran chilled in an ice bath was added a solution of 5.16 g of 4-(4-chlorophenyloxy)benzene-sulfonyl chloride in 50 ml of tetrahydrofuran and 20 ml of CH2Cl2. The mixture was refluxed for 2 hours and the solvent removed under vacuum and the residue partitioned between CH2Cl2·H2O (1:1). The CH2Cl2 layer was separated and washed with 2 N citric acid, brine and dried (Na2SO4). The solution was filtered through a thin pad of hydrous magnesium silicate and the filter pad washed with CH2Cl2. The filtrate was concentrated to give 4.5 g of N-methyl-4-(4-chlorophenoxy)benzene-sulfonamide as a yellow solid, m.p. 80-83° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customthe solvent removed under vacuum
  3. customthe residue partitioned between CH2Cl2·H2O (1:1)
  4. customThe CH2Cl2 layer was separated
  5. washwashed with 2 N citric acid, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationThe solution was filtered through a thin pad of hydrous magnesium silicate
  8. washthe filter pad washed with CH2Cl2
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2fb4db9ea22343bd886d76dac59f9c62
Source dataset
uspto-grants-2002_12
Patent number
US06498167B2

Reaction notes

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