Acetic Anhydride → HCID 54312022, compound

HRID 1725573Notes

Reaction equation

HRID 1725573 reaction equation
[NH2:1][C:2]1[S:11][C:5]2[CH2:6][N:7]([CH3:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[C:17]([O:20][C:21](=O)C)(=O)[CH3:18]>C(OCC)(OCC)OCC>[CH2:17]([O:20][CH:21]=[N:1][C:2]1[S:11][C:5]2[CH2:6][N:7]([CH3:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 207319ethyl 2-amino-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate

Product 1

HCID 54312022HCID 54312022, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

40.0 g (167 mM) of 2-amino-3-carboethoxy-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine in 250 ml of triethyl orthoformate were mixed with 3.2 ml of acetic anhydride and refluxed under nitrogen for 3 h. The mixture was then concentrated completely in a rotary evaporator at 80° C. 48.0 g (97%) of crude product were isolated as a dark oil which is sufficiently pure for further reaction.

Workup

  1. temperaturerefluxed under nitrogen for 3 h
  2. concentrationThe mixture was then concentrated completely in a rotary evaporator at 80° C

Sources & evidence

ORD record
ord-105e5d32f6de416e879aada56d05e888
Source dataset
uspto-grants-2009_02
Patent number
US07491729B2

Reaction notes

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