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

HRID 239847

반응식

HRID 239847 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 67553Tetrabutylammonium Iodide촉매HCID 8471Triethylamine용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-8063ddaf989144d4a772fce440c3c85f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642808B2

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