Hydrochloric Acid → HCID 20464717, compound

HRID 325422Notes

Reaction equation

HRID 325422 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:21](=[O:27])[C:22]([O:24]CC)=[O:23])[N:13]([CH3:20])[C:14]=2[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:21](=[O:27])[C:22]([OH:24])=[O:23])[N:13]([CH3:20])[C:14]=2[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20464728HCID 20464728, compound

Product 1

HCID 20464717HCID 20464717, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4(m-chlorophenylthio)methyl-5-ethoxycarbonyl-1-methyl-α-oxopyrrole-2-acetate (1.28 g, 3.1 mmol) is dissolved in refluxing ethanol (10 ml) and 2.5 N aqueous sodium hydroxide (9 ml, 22.5 mmol) is added. The mixture is heated at reflux for 1.5 hours after the solution becomes homogeneous, then it is cooled in ice and acidified to pH 2.0 with 6 N aqueous HCl. The resulting solid is collected, filtered and dried to give 1.00 g of 4-(m-chlorophenylthio)methyl-5-hydroxycarbonyl-1-methyl-α-oxopyrrole-2-acetic acid.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 1.5 hours after the solution
  4. temperatureit is cooled in ice
  5. customThe resulting solid is collected
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-96d83c84adb14235b837c6d69ae574e0
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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