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

HRID 493091ノート

反応式

HRID 493091 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-501c694997154012851406d742a8a38e
出典データセット
uspto-grants-2009_05
特許番号
US07534791B2

反応ノート

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