Ammonium Chloride → Ethyl 3-chloro-4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 1368980Notes

Reaction equation

HRID 1368980 reaction equation
[Cl: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]([Cl: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 109971824-chlorothiophene-2-carbaldehyde

Product 1

HCID 57348924Ethyl 3-chloro-4H-thieno[3,2-b]pyrrole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-thiophene-2-carbaldehyde (Iriarte, J.; Martinez, E.; Muchowski, J. M., J. Heterocycl. Chem., 13: 393-4 (1976)) was annulated according to Procedure H (aldehyde and azido-acetic acid ethyl ester added as ethanol solution (1.2 M of ester) such that reaction temperature maintained at 0° C.; reaction mixture allowed to warm to 10° C., stirred for 1.5 h, poured into cold saturated aqueous NH4Cl; after ether extractions, combined acrylate organic phases washed with water until aqueous phase was neutral; acrylate not purified).

Workup

  1. customreaction mixture
  2. temperatureto warm to 10° C.
  3. extractionafter ether extractions
  4. washwashed with water until aqueous phase
  5. customacrylate not purified)

Sources & evidence

ORD record
ord-21601d6471cf4d84ae9396fbf637e448
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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