Methyl iodide → HCID 10634234, compound

HRID 2193902Notes

Reaction equation

HRID 2193902 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].I[CH3:18]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH3:18])=[O:4]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Product 1

HCID 10634234HCID 10634234, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl-3-amino-5-phenylthiophene-2-carboxylate (200 mg, 0.855 mmol) in anhydrous N,N-dimethylformamide (4.6 ml) were added 4.2 ml (8.55 mmol) of 2M iodomethane solution in t-buthylmethylether. The mixture was stirred at 60° C. for 18 hours, concentrated and purified using biotage technics (silica gel, hexane to hexane:ethyl acetate; 95:5 containing few drops of triethylamine) to give 68 mg (32% yield) of 3-methylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester. 1H NMR (CDCl3, 400 MHz) 7.65-7.62 (m, 2H), 7.42-7.36 (m, 3H), 6.86 (broad s, 1H), 3.83 (s, 3H), 3.04 (d, 3H)

Workup

  1. concentrationconcentrated
  2. custompurified

Sources & evidence

ORD record
ord-9f7fa1ac34cb4afd90f23633b0500493
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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