Methylamine → Methyl-[2-(2-methyl-benzo[b]thiophen-3-ylsulfanyl)-benzyl]-amine

HRID 493091노트

반응식

HRID 493091 반응식
CS(Cl)(=O)=O.[CH3:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]O.[CH2:25]([N:27](CC)CC)C.CN.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:25][NH:27][CH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[S:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[S:11][C:7]=1[CH3:6]

참가 물질

7

반응물 5

HCID 6329MethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68898143[2-(2-Methyl-benzo[b]thiophen-3-ylsulfanyl)-phenyl]-methanol

생성물 1

HCID 15982430Methyl-[2-(2-methyl-benzo[b]thiophen-3-ylsulfanyl)-benzyl]-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Methanesulfonyl chloride (170 μL, 2.2 mmol) is added to a solution of [2-(2-Methyl-benzo[b]thiophen-3-ylsulfanyl)-phenyl]-methanol (590 mg, 2.1 mmol) and triethyl amine (350 μL, 2.5 mmol) in 10 mL dry THF at 0° C. under an argon atmosphere. The reaction mixture is stirred for 1 hour at room temperature and cooled to 0° C. 2 M methyl amine in THF is added and the reaction is stirred at room temperature for 3 hours. Saturated aqueous NaHCO3 is added and the mixture is extracted with ethyl acetate. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography on silica gel using ethyl acetate and then ethyl acetate-methanol-triethyl amine (3:1:1) as eluents. This furnishes 460 mg (75%) of the title compound as an oil.

후처리

  1. temperaturecooled to 0° C
  2. stirringthe reaction is stirred at room temperature for 3 hours
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-501c694997154012851406d742a8a38e
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534791B2

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