Ammonia → 4H-Thieno[3,2-b]pyrrole-5-carboxamide

HRID 746597Notes

Reaction equation

HRID 746597 reaction equation
C([O:3][C:4]([C:6]1[NH:10][C:9]2[CH:11]=[CH:12][S:13][C:8]=2[CH:7]=1)=O)C.[NH3:14].[OH-].[Li+]>CO>[S:13]1[C:8]2[CH:7]=[C:6]([C:4]([NH2:14])=[O:3])[NH:10][C:9]=2[CH:11]=[CH:12]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3939Lithium HydroxideHCID 292163ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 185243894H-Thieno[3,2-b]pyrrole-5-carboxamideYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Add to 4H-thieno[3,2-b]pyrrole-5-carboxylic acid ethyl ester (1.74 gm, 8.9 mmol) and 7M ammonia in methanol (100 ml) in a steel bomb a chip of lithium hydroxide (0.1 gm). Seal the bomb and heat to 100° C. for 16 hrs. Cool to room temperature, and concentrate to remove the volatiles. Purify the crude product via flash chromatography (ISCO, silica cartridge, 40 gm, elute with methanol 0-5% in methylene chloride) to provide the title compound (560 mg, 38%) as an off-white solid.

Workup

  1. customSeal the bomb
  2. temperatureCool to room temperature
  3. concentrationconcentrate
  4. customto remove the volatiles
  5. customPurify the crude product
  6. washvia flash chromatography (ISCO, silica cartridge, 40 gm, elute with methanol 0-5% in methylene chloride)

Sources & evidence

ORD record
ord-b01fd6b914a74b818cce0bccc8b00ab1
Source dataset
uspto-grants-2008_07
Patent number
US07393867B2

Reaction notes

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