Triethylamine → 3-Chloro-4-({[3-chloro-4-(trifluoromethyl)benzyl]amino}carbonyl)benzenesulfonyl chloride

HRID 1808200Notes

Reaction equation

HRID 1808200 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([Cl:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25])[CH2:19][NH2:20].CCN(CC)CC>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([S:11]([Cl:14])(=[O:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:20][CH2:19][C:18]1[CH:21]=[CH:22][C:23]([C:24]([F:25])([F:26])[F:27])=[C:16]([Cl:15])[CH:17]=1)=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 198147312-Chloro-4-(chlorosulfonyl)benzoyl chlorideHCID 235127443-Chloro-4-(trifluoromethyl)benzylamine

Product 1

HCID 577321163-Chloro-4-({[3-chloro-4-(trifluoromethyl)benzyl]amino}carbonyl)benzenesulfonyl chlorideYield 40.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-4-(chlorosulfonyl)benzoyl chloride (J. Org. Chem, 56, 16, 1991, 4974) (300 mg, 0.877 mmol, 1 eq) in DCM (3 ml) was added 3-chloro-4-(trifluoromethyl)benzylamine (175 mg, 0.835 mmol, 0.95 eq) and Et3N (33 mg, 0.32 mmol, 0.37 eq) and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (10 ml), washed with water (10 ml), dried over sodium sulphate, filtered and evaporated. The crude material was purified by column chromatography eluting with ethyl acetate to yield the title compound (154 mg, 0.34 mmol, 39%).

Workup

  1. washwashed with water (10 ml)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by column chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-11d118631a774cb58f646d9633e23795
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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