Dichloromethane → N-(2-Benzoyl-4-chloro-phenyl)-4-phenylethynyl-benzenesulfonamide

HRID 239847

Reaction equation

HRID 239847 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)(=[O:19])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.COCCOC.[C:36]1([C:42]#[CH:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cu]I.C(N(CC)CC)C>[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([C:43]#[C:42][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 10821PhenylacetyleneHCID 3334757N-(2-benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamide

Product 1

HCID 11328918N-(2-Benzoyl-4-chloro-phenyl)-4-phenylethynyl-benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 8471TriethylamineSolvent

Procedure

To a magnetically stirred mixture of the N-(2-Benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamide (450 mg, 1.0 mmol), [1,1′ Bis-(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (30 mg, 0.037 mmol) and copper (I) iodide (100 mg, 0.52 mmol) was added DME (6 mL) and dry triethylamine (3 mL) under dry nitrogen. To this stirred mixture was added tetrabutylammonium iodide (250 mg), followed by the addition of phenylacetylene (0.240 mL). The dark green mixture was stirred at ambient temp overnight. The reaction was worked up by addition to crushed ice and extracted with ethyl acetate (3×75 mL), and the organic layer was dried (MgSC4), filtered and concentrated. The crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane. 1H NMR (CDCl3) δ 9.64 (br s, 1H, NH), 7.75 (d, 1H, J=Hz), 7.75 (d, 1H, J=8.8 Hz), 7.48 (m, 8H), 7.36 (m, 7H). MS: m/z 472 (M+1)

Workup

  1. additionThe reaction was worked up by addition
  2. customto crushed ice
  3. extractionextracted with ethyl acetate (3×75 mL)
  4. dry with materialthe organic layer was dried (MgSC4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane

Sources & evidence

ORD record
ord-8063ddaf989144d4a772fce440c3c85f
Source dataset
uspto-grants-2014_02
Patent number
US08642808B2

Linked notes

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