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

HRID 18900

反応式

HRID 18900 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 67553Tetrabutylammonium Iodide触媒HCID 8471Triethylamine溶媒

実験手順

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 (MgSO4), 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)

後処理

  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 (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane

出典と根拠

ORDレコード
ord-903e7510157140739b126551ce0c9cd1
出典データセット
uspto-grants-2010_06
特許番号
US07741519B2

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