Hydrochloric Acid → 6-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505806Notes

Reaction equation

HRID 505806 reaction equation
[S:1]1[C:8]2[CH:7]=[CH:6][NH:5][C:4]=2[CH:3]=[C:2]1[C:9]([O:11]CC)=[O:10].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[O-]CC.[Na+].Cl>CCO>[C:14]1([C:7]2[C:8]3[S:1][C:2]([C:9]([OH:11])=[O:10])=[CH:3][C:4]=3[NH:5][CH:6]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 2723922Sodium ethoxideHCID 25258328ethyl 4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 586790836-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution (0.25 M) of ethyl 4H-thieno[3,2-b]pyrrole-2-carboxylate in EtOH was treated with cyclohexanone (2 eq.) and sodium ethoxide (2.05 eq.) then heated to reflux for 4 h. After cooling down, it was acidified with aqueous HCl (6 N) and the precipitate was filtered and dried, affording the title compound (98%) as a solid.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling down
  4. filtrationthe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-3ce9577b9f8743c7af7f1fde928b1060
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

Loading…