Ethanol → HCID 13457765, compound

HRID 462762Notes

Reaction equation

HRID 462762 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]([CH3:17])C(=O)OCC)[CH:8]=[CH:9][CH:10]=1)=[O:5].[OH-].[Na+].[CH2:24](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][CH3:17])[C:8]([CH3:24])=[CH:9][CH:10]=1)=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13457751HCID 13457751, compound

Product 1

HCID 13457765HCID 13457765, compound

Procedure

A solution containing [2-(2-chlorobenzoyl)-1H-pyrrol-1-yl]-methyl-carbamic acid, ethyl ester (29.4 g, 91 mmol) and sodium hydroxide (11 g, 275 mmol) in 50% aqueous ethanol was heated under reflux for 16 hours. The excess ethanol was evaporated and the solution was adjusted to pH 7 with 10% HCl. The resultant slurry was extracted with three 100 ml portions of DCM, dried (MgSO4), filtered, and evaporated to give 22 g of solid. This solid was charcoaled and recrystallized from ether-hexane to give 21 g (93%) of powder, m.p. 107°-108°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customThe excess ethanol was evaporated
  4. extractionThe resultant slurry was extracted with three 100 ml portions of DCM
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-bd66db8d3fff4a5c8c4ac9ceb31b7d47
Source dataset
uspto-grants-1985_05
Patent number
US04517195

Reaction notes

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