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

HRID 493091Notes

Reaction equation

HRID 493091 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-501c694997154012851406d742a8a38e
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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