4-Chlorophenol → HCID 18669510, compound

HRID 1058988Notes

Reaction equation

HRID 1058988 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19]Br)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][O:36][C:33]2[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 10551830HCID 10551830, compound

Product 1

HCID 18669510HCID 18669510, compoundYield 100.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N,N-dibenzyl-4-(2-bromoacetyl)benzenesulfonamide (10.5 g, 23 mmoles), and p-chlorophenol (2.94 g, 23 mmoles) in methylene chloride (42 ml), potassium carbonate (4.83 g, 34.7 mmoles) and tetrabutylammonium bromide (0.42 g, 1.2 mmoles) in water (140 ml)was added. The reaction mixture was refluxed for 16 hours. After cooling, the mixture was diluted with methylene chloride (150 ml). The organic layer was separated, washed with water, and dried (Na2SO4) The solvent was removed under reduced pressure. N,N-dibenzyl-4-[2-(4-chlorophenoxy)acetyl]benzenesulfonamide (11.7 g) was obtained as a semisolid residue, which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. temperatureAfter cooling
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (Na2SO4) The solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-35e2601fbfe44f2fbe17e0a2fad0a240
Source dataset
uspto-grants-2003_02
Patent number
US06518303B2

Reaction notes

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