Methyl Acrylate → HCID 23369385, compound

HRID 446721Notes

Reaction equation

HRID 446721 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH2:10]>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][CH2:10][CH2:9][C:8]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 34005(2-Thienylmethyl)amine

Product 1

HCID 23369385HCID 23369385, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of thiophen-2-ylmethanamine (20.0 g, 176.7 mmol) in ethanol (1 L) at 0° C. was added methyl acrylate (15.21 g, 176.7 mmol). The reaction was allowed to warm to room temperature overnight, at which point HPLC analysis indicated that the reaction was complete. The solvent was removed in vacuo to give methyl 3-(thiophen-2-ylmethylamino)propanoate (Compound 1040) as a pale tan oil (35.21 g, 99%); 1H NMR (300 MHz, CDCl3): δ 7.28 (s, CHCl3), 7.22 (dd, J=1.5, 4.7 Hz, 1H), 6.97-6.95 (m, 2H), 4.16 (q, J=7.1 Hz, 2H), 4.02 (s, 3H), 3.69 (d, J=5.0 Hz, 2H), 2.95 (t, J=6.5 Hz, 2H) and 2.57-2.48 (m, 2H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f06bec1231424aa091c86d3319337ca4
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

Loading…