Acetic Anhydride → 2-Ethoxymethyleneamino-3,5-dicarbethoxy-4,6-dihydrothieno[3,2-c]pyrrole

HRID 1935466Notes

Reaction equation

HRID 1935466 reaction equation
[C:1]([O:4][C:5](=O)C)(=O)[CH3:2].[NH2:8][C:9]1[S:16][C:15]2[CH2:14][N:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][C:11]=2[C:10]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(OCC)(OCC)OCC>[CH2:1]([O:4][CH:5]=[N:8][C:9]1[S:16][C:15]2[CH2:14][N:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][C:11]=2[C:10]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22464559Diethyl 2-amino-4,6-dihydro-5H-thieno[2,3-c]pyrrole-3,5-dicarboxylate

Product 1

HCID 544107892-Ethoxymethyleneamino-3,5-dicarbethoxy-4,6-dihydrothieno[3,2-c]pyrroleYield 99%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

0.3 ml of acetic anhydride was added to 1.4 g (4.8 mmol) of 2-amino-3,5-dicarboethoxy-4,6-dihydrothieno[3,2-c]pyrrole in 14 ml of triethyl orthoformate, and the mixture was boiled under nitrogen and at reflux for 1 h. After that, the mixture was evaporated right down at 80° C. on a rotary evaporator. 1.6 g (99%) of crude product were isolated as a viscous oil, which is sufficiently pure for further reaction.

Workup

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

Sources & evidence

ORD record
ord-5ee73b9fac814f02a55cc1666870ec5b
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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