Ammonium Chloride → ETHYL 3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE

HRID 1368985Notes

Reaction equation

HRID 1368985 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.[CH2:9]([O:11][C:12](=[O:17])[CH2:13][N:14]=[N+]=[N-])[CH3:10].[NH4+].[Cl-]>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[NH:14][C:3]2[C:2]([CH3:1])=[CH:6][S:5][C:4]=2[CH:7]=1)=[O:17])[CH3:10]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 27955264-methylthiophene-2-carbaldehyde

Product 1

HCID 11651387ETHYL 3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methyl-thiophene-2-carbaldehyde (Detty, M. R.; Hays, D. S., Heterocycles, 40: 925-37 (1995)) was annulated according to Procedure H (aldehyde and azido-acetic acid ethyl ester added as ethanol solution (1.1 M of ester); reaction poured into cold saturated aqueous NH4Cl; after ether extractions, acrylate organic phase washed with water until aqueous phase was neutral; acrylate not purified).

Workup

  1. customreaction
  2. extractionafter ether extractions, acrylate organic phase
  3. washwashed with water until aqueous phase
  4. customacrylate not purified)

Sources & evidence

ORD record
ord-5a19c35d777a4a70ba316e3cdbb1c2f3
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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