Water → HCID 13457754, compound

HRID 280126Notes

Reaction equation

HRID 280126 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([C:6]1[N:7]([N:11](C)[C:12](=O)OCC)[CH:8]=[CH:9][CH:10]=1)=[O:5].O.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([C:6]1[N:7]([NH:11][CH3:12])[CH:8]=[CH:9][CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13457751HCID 13457751, compound

Product 1

HCID 13457754HCID 13457754, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2-(2-Chlorobenzoyl)-1H-pyrrol-1-yl]-methyl-carbamic acid, ethyl ester (39.2 g, 0.127 mol) was dissolved in 100 ml of ethanol and 200 ml of H2O containing sodium hydroxide (25 g, 0.625 mol). The reaction was refluxed for 18 hours followed by evaporation of the ethanol. The aqueous solution was extracted with three 300 ml portions of ethyl acetate, dried (MgSO4), filtered, and evaporated to give 28 g of an oil. This oil was distilled via Kugelrohr apparatus 125° (0.15 mmHg) to give 26.3 g of a solid. This solid was triturated with hexane to give 25.5 g (85%) of crystals, m.p. 56°-58°.

Workup

  1. temperatureThe reaction was refluxed for 18 hours
  2. customfollowed by evaporation of the ethanol
  3. extractionThe aqueous solution was extracted with three 300 ml portions of ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-920887af67154f848a954690784215e8
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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