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

HRID 1935458Notes

Reaction equation

HRID 1935458 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)[CH3:2].[NH2:8][C:9]1[S:17][C:12]2[CH2:13][NH:14][CH2:15][CH2:16][C:11]=2[C:10]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[C:23](OCC)(OCC)(OCC)C>>[C:18]([C:10]1[C:11]2[CH2:16][CH2:15][N:14]([CH3:23])[CH2:13][C:12]=2[S:17][C:9]=1[N:8]=[C:1]([O:4][CH2:5][CH3:6])[CH3:2])([O:20][CH2:21][CH3:22])=[O:19]

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 93%

Procedure

0.8 ml of acetic anhydride was added to 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 and the mixture was boiled under nitrogen and at reflux for 2 h. After that, the mixture was evaporated right down at 80° C. on a rotary evaporator. 3.6 g (93%) of crude product were isolated as a dark oil, which is sufficiently pure for further reaction.

Workup

  1. temperatureat reflux for 2 h
  2. customAfter that, the mixture was evaporated right down at 80° C. on a rotary evaporator

Sources & evidence

ORD record
ord-040096e4e7ab4db5a3658d54109acac4
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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