Triethylamine → 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-benzenesulfonamide

HRID 2242809Notes

Reaction equation

HRID 2242809 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].CCN(CC)CC.[C:14]([C:16]1[CH:17]=[CH:18][C:19]([O:26][C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=2)=[C:20]([S:22](Cl)(=[O:24])=[O:23])[CH:21]=1)#[N:15]>C(Cl)Cl>[C:14]([C:16]1[CH:17]=[CH:18][C:19]([O:26][C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=2)=[C:20]([S:22]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])(=[O:23])=[O:24])[CH:21]=1)#[N:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 592082825-Cyano-2-(3,5-dichlorophenoxy)phenylsulfonylchloride

Product 1

HCID 592083045-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-benzenesulfonamideYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of N1,N1-dimethyl-ethane-1,2-diamine (74.0 mg, 0.84 mmol) and Et3N in dry CH2Cl2 (3 ml) was added the solution of 5-cyano-2-(3,5-dichlorophenoxy)phenylsulfonylchloride (90%, 282 mg, 0.7 mmol) in dry CH2Cl2 (6 ml) dropwise. The resulting solution was stirred at room temperature for 1 hour. CH2Cl2 (60 ml) was added and the mixture was washed with water, brine, and dried over MgSO4. The solvent was evaporated, and the residue was purified by column chromatography (CH2Cl2/CH3OH=10:1) to give 5-cyano-2-(3,5-dichloro-phenoxy)-N-(2-dimethylamino-ethyl)-benzene-sulfonamide as white solid (220 mg, 75.9%): HPLC-MS (ESI): Calcd for C19H21Cl2N3O4S [M+H]+ 414, Found: 414

Workup

  1. washthe mixture was washed with water, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography (CH2Cl2/CH3OH=10:1)

Sources & evidence

ORD record
ord-b3181ef8fab74b65ae7d0fec486d06e4
Source dataset
uspto-grants-2010_03
Patent number
US07674797B2

Reaction notes

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