Methylamine → HCID 68897026, compound

HRID 493101Notes

Reaction equation

HRID 493101 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[S:13]1[CH:17]=[C:16]([S:18][C:19]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:20]=2[C:21](O)=[O:22])[C:15]2[CH:29]=[CH:30][CH:31]=[CH:32][C:14]1=2.CN.C(OCC)(=O)C>C1COCC1>[S:13]1[CH:17]=[C:16]([S:18][C:19]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:20]=2[C:21]([NH:3][CH3:1])=[O:22])[C:15]2[CH:29]=[CH:30][CH:31]=[CH:32][C:14]1=2

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 68900017HCID 68900017, compound

Product 1

HCID 68897026HCID 68897026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (324 mg, 2 mmol) is added to 2-(benzo[b]thiophen-3-ylsulfanyl)-5-methyl-benzoic acid (300 mg, 1 mmol) in mL dry THF and stirred for 2 hours at room temperature. 2.5 mL methyl amine (2M in THF, 5 mmol) is added and the reaction mixture is stirred for 16 hours at room temperature. Ethyl acetate is added and the organic phase is washed with 1 N HCl (aq) and brine, dried with MgSO4 and concentrated in vacuo to give the title compound, which is used in the next step without further purification.

Workup

  1. stirringthe reaction mixture is stirred for 16 hours at room temperature
  2. washthe organic phase is washed with 1 N HCl (aq) and brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7e5daf6bb6c4ec0afc824bb587b0bc1
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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