Acetic Anhydride → Ethyl n-(3-carboethoxy-6-methyl-4,5,6,7-tetrahydrothieno-[2,3-c]pyridin-2-yl)ethaneimidate

HRID 325072Notes

Reaction equation

HRID 325072 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16]([O:19][C:20](=O)[CH3:21])(=O)[CH3:17].[C:23](OCC)(OCC)(OCC)C>>[C:11]([C:3]1[C:4]2[CH2:9][CH2:8][N:7]([CH3:23])[CH2:6][C:5]=2[S:10][C:2]=1[N:1]=[C:16]([O:19][CH2:20][CH3:21])[CH3:17])([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 66221Triethyl orthoacetateHCID 212359Thieno(2,3-c)pyridine-3-carboxylic acid, 4,5,6,7-tetrahydro-2-amino-, ethyl ester,

Product 1

HCID 54227348Ethyl n-(3-carboethoxy-6-methyl-4,5,6,7-tetrahydrothieno-[2,3-c]pyridin-2-yl)ethaneimidateYield 92%

Procedure

3.0 g (12.5 mmol) of 2-amino-3-carboethoxy-4,5,6,7-tetrahydrothieno[2,3-c]pyridine in 25 ml of triethyl orthoacetate were mixed with 0.8 ml of acetic anhydride and refluxed under nitrogen for 2 h. The mixture was then completely evaporated in a rotary evaporator at 80° C. 3.6 g (92%) of crude product were isolated as a dark oil which is sufficiently pure for the next reaction.

Workup

  1. temperaturerefluxed under nitrogen for 2 h
  2. customThe mixture was then completely evaporated in a rotary evaporator at 80° C

Sources & evidence

ORD record
ord-510aafaf92e644769172c91b73bb85f5
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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