Sodium Hydroxide → HCID 15591625, compound

HRID 365114Notes

Reaction equation

HRID 365114 reaction equation
C([O:3][C:4]([C:6]1[S:27][C:9]2[NH:10][C:11]([C:22]([O:24]CC)=[O:23])=[C:12]([C:13](=[O:21])[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[C:8]=2[C:7]=1[CH3:28])=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([C:6]1[S:27][C:9]2[NH:10][C:11]([C:22]([OH:24])=[O:23])=[C:12]([C:13](=[O:21])[C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[C:8]=2[C:7]=1[CH3:28])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15591624HCID 15591624, compound

Product 1

HCID 15591625HCID 15591625, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

105 g of crude 2,5-diethoxycarbonyl-3-methyl-4-parachlorobenzoylthieno[2,3-b]pyrrole are heated at reflux in a mixture of 1 liter of ethanol and 1 liter of a normal solution of sodium hydroxide until complete saponification. The ethanol is then eliminated by distillation on a water bath. The aqueous solution is filtered and then acidified. The resulting precipitate is collected by filtration, washed with water, and dried with air and then in vacuo. In this manner, 92 g of crude 2,5-dicarboxy-3-methyl-4-parachlorobenzoylthieno[2,3-b]pyrrole are obtained, which is used in subsequent syntheses without further purification. The following were obtained in the same manner:

Workup

  1. distillationThe ethanol is then eliminated by distillation on a water bath
  2. filtrationThe aqueous solution is filtered
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with water
  5. customdried with air

Sources & evidence

ORD record
ord-368c5b115a634879a92da497e28fe187
Source dataset
uspto-grants-1986_08
Patent number
US04608384

Reaction notes

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