Methylamine → 2-(Methylaminomethyl)thieno[2,3-b]thiophene

HRID 1761055Notes

Reaction equation

HRID 1761055 reaction equation
[S:1]1[C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=[C:2]1[C:9](OCC)=O.[CH3:14][NH2:15]>CO>[CH3:14][NH:15][CH2:9][C:2]1[S:1][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22593799Ethyl thieno[2,3-b]thiophene-2-carboxylate

Product 1

HCID 225937092-(Methylaminomethyl)thieno[2,3-b]thiopheneYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of ethyl thieno[2,3-b]thiophene-2-carboxylate (3.84 g, 18.1 mmole) in 40% aqueous CH3NH2 (100 mL) and MeOH (10 mL) was stirred at RT for 18 hr. During that time the suspension became a solution. The mixture was concentrated to approximately ⅓ volume at which time the product precipitated. The solid was collected by filtration, washed with H2O, and dried in vacuo to give the title compound (3.01 g, 85%): 1H NMR (400 MHz, d6-DMSO) δ 8.60 (bs,1H), 7.92 (s,1H), 7.67 (d, J=5.2 Hz, 1H), 7.38 (d, J=5.2 Hz,1H), 2.78 (d, J=4.6 Hz. 3H).

Workup

  1. concentrationThe mixture was concentrated to approximately ⅓ volume at which time the product
  2. customprecipitated
  3. filtrationThe solid was collected by filtration
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1e1706a7648c45b784f4e78761bebf7b
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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