p-Ethynyltoluene → N-(4-p-Tolylethynyl-phenyl)-methanesulfonamide

HRID 1716302노트

반응식

HRID 1716302 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)#[CH:14]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([C:13]#[C:14][C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=2)=[CH:16][CH:17]=1

참가 물질

5

반응물 2

HCID 13018p-EthynyltolueneHCID 836147N-(4-iodophenyl)methanesulfonamide

생성물 1

HCID 68511472N-(4-p-Tolylethynyl-phenyl)-methanesulfonamide

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

실험 절차

A mixture of N-(4-iodo-phenyl)-methanesulfonamide (0.46 g, 1.54 mmol), Pd(PPh3)2Cl2 (54 mg, 0.077 mmol) and CuI (14.7 mg, 0.077 mmol) in TEA/THF (10 mL/3 mL) was treated with 1-ethynyl-4-methyl-benzene (0.29 mL, 2.32 mmol). The reaction mixture was degassed and stirred at room temperature for 30 min. The solvent was removed under the reduced pressure. The residue was diluted with EtOAc and water. After the usual work-up, the obtained crude material was purified by chromatography (35% EtOAc/hexanes) to give the desired product. MS (EI) 286 (M+H)+.

후처리

  1. customThe reaction mixture was degassed
  2. customThe solvent was removed under the reduced pressure
  3. additionThe residue was diluted with EtOAc and water
  4. customAfter the usual work-up, the obtained crude material
  5. customwas purified by chromatography (35% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ea964cb07ad841b485d353a6aeb19a31
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803793B2

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