Pyrrole-2-carboxaldehyde → HCID 9921396, compound

HRID 1860250Notes

Reaction equation

HRID 1860250 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([NH2:12])=[O:11])=[CH:9][C:4]=2[CH2:3]1.[NH:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=O>N1CCCCC1.CC(O)C>[O:1]=[C:2]1[NH:6][C:5]2[S:7][C:8]([C:10]([NH2:12])=[O:11])=[CH:9][C:4]=2/[C:3]/1=[CH:18]/[C:14]1[NH:13][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 18626983HCID 18626983, compound

Product 1

HCID 9921396HCID 9921396, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8082PiperidineSolvent

Conditions

Temperature
75 °C

Procedure

5,6-Dihydro-5-oxo-4H-thieno[2,3-b]pyrrole-2-carboxamide (30 mg, 0.17 mmol) was dissolved in a solution of 1% piperidine in 2-propanol (2 ml). Pyrrole-2-carboxaldehyde (16 mg, 0.18 mmol) was added in one portion and the mixture heated at 75° C. for 1 hour. The reaction mixture was poured into an ice/water mixture (10 ml) and the precipitated solid was collected by filtration and washed with water to give 15 mg of (Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxamide as a yellow/brown solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-8b5fb51f5d0f406c9f50f0e68870f86a
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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