p-Toluenesulfonic acid → (Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylic acid

HRID 1860266Notes

Reaction equation

HRID 1860266 reaction equation
O1CCCCC1ON[C:9]([C:11]1[S:25][C:14]2[NH:15][C:16](=[O:24])/[C:17](=[CH:18]\[C:19]3[NH:20][CH:21]=[CH:22][CH:23]=3)/[C:13]=2[CH:12]=1)=[O:10].C1(C)C=CC(S(O)(=O)=[O:33])=CC=1>CO>[O:24]=[C:16]1[NH:15][C:14]2[S:25][C:11]([C:9]([OH:10])=[O:33])=[CH:12][C:13]=2/[C:17]/1=[CH:18]/[C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86584528(Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno [2,3-b]pyrrole-2-carboxylic acid (tetrahydro-pyran-2-yloxy)-amide

Product 1

HCID 69844590(Z)-5,6-dihydro-5-oxo-4-[(1H-pyrrol-2-yl)methylene]-4H-thieno[2,3-b]pyrrole-2-carboxylic acidYield 42.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno[2,3-b]pyrrole-2-carboxylic acid (tetrahydro-pyran-2-yloxy)-amide (65 mg, 0.18 mmol) was dissolved in methanol (2 ml). 4-Toluene sulfonic acid (0.09 mmol, 15 mg) was added in one portion and the solution stirred at room temperature for 2 hours. The solvent was evaporated and the residue triturated with diethyl ether to give 10 mg of (Z)-5-Oxo-4-[1H-pyrrol-2-ylmethylene]-5,6-dihydro-4H-thieno[2,3-b]pyrrole-2-carboxylic acid hydroxamide as a brown solid. MS(ES): m/e 276 [M+H].

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-d497da55914740a08a027a054d451865
Source dataset
uspto-grants-2003_03
Patent number
US06528653B2

Reaction notes

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