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

Participants

Role	Name	HCID	Charge
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	Acetic acid, azido-, ethyl ester	HCID 69480	—
Reactant	1-Hydroxyethyl radical	HCID 119440	—
Reactant	5-Chloro-4-methyl-2-thiophenecarboxaldehyde	HCID 22610271	—
Solvent	Ethanol	HCID 702	—
Product	ETHYL 2-CHLORO-3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE	HCID 11521594	—

Reaction Conditions

Temperature	10 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06399601B1
Source dataset	uspto-grants-2002_06
ORD ID	ord-66b7a6330b4340e0921337d827350107
Source note	uspto-grants-2002_06