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

HRID 1368990Notes

Reaction equation

HRID 1368990 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][C:3]=1[CH3:9].[CH2:10]([O:12][C:13](=[O:18])[CH2:14][N:15]=[N+]=[N-])[CH3:11].[O-]CC.[NH4+].[Cl-]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[NH:15][C:4]2[C:3]([CH3:9])=[C:2]([Cl:1])[S:6][C:5]=2[CH:7]=1)=[O:18])[CH3:11]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 1194401-Hydroxyethyl radicalHCID 226102715-Chloro-4-methyl-2-thiophenecarboxaldehyde

Product 1

HCID 11521594ETHYL 2-CHLORO-3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

5-Chloro-4-methyl-thiophene-2-carbaldehyde was annulated according to Procedure H (aldehyde and azido-acetic acid ethyl ester was added as ethanol solution (1 M of ester) to −20° C. ethoxide solution; allow to warm to 10° C. over 2 h, 10° C. 2 h; reaction poured into cold saturated aqueous NH4Cl; after ether extraction, acrylate organic phase washed with water until aqueous phase was neutral; solution of crude acrylate added to refluxing xylenes over 5 min and then heated at reflux).

Workup

  1. custom2 h
  2. customreaction
  3. extractionafter ether extraction, acrylate organic phase
  4. washwashed with water until aqueous phase
  5. additionsolution of crude acrylate added
  6. temperatureto refluxing xylenes over 5 min
  7. temperatureheated
  8. temperatureat reflux)

Sources & evidence

ORD record
ord-74ab9be43c4b46989c31ac8b2c1bb5b4
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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