Ammonium Chloride → 3-Bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 1368982Notes

Reaction equation

HRID 1368982 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.C([O:11][C:12](=[O:17])[CH2:13][N:14]=[N+]=[N-])C.[NH4+].[Cl-]>C(O)C>[Br:1][C:2]1[C:3]2[NH:14][C:13]([C:12]([OH:17])=[O:11])=[CH:7][C:4]=2[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 225564983-Bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-thiophene-2-carbaldehyde 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 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-473ce265403c4191adbafd5fe34dbb1d
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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