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Tetrahydrofuran → 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

HRID 453586
Notes
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Reaction equation

HRID 453586 reaction equation
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([O:12]CC)=[O:11])[NH:5][C:4]=2[C:3]=1[N:15]([CH3:24])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17].O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([OH:12])=[O:11])[NH:5][C:4]=2[C:3]=1[N:15]([CH3:24])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59411376ethyl 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 594113852-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ethyl 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylate (8.39 g), tetrahydrofuran (50 mL) and ethanol (50 mL) was added 8N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated, 6N hydrochloric acid was added to the obtained residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. Crystallization from diethyl ether gave 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid (7.07 g, yield 91%) as brown crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition6N hydrochloric acid was added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-e882d971e98d48fca68378e25c0152a7
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492405B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes