Sodium Hydroxide → 4-(3-(Cyclopropylmethyl)ureido)benzoic acid

HRID 408862Notes

Reaction equation

HRID 408862 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:19])[NH:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([CH2:4][NH:5][C:6](=[O:19])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:17][CH:18]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3830959Ethyl 4-(3-(cyclopropylmethyl)ureido)benzoate

Product 1

HCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(3-(cyclopropylmethyl)ureido)benzoate (55.3 mmol, 14.5 g) was suspended in ethanol (400 ml) and 4M sodium hydroxide (332 mmol, 83 mL) added. The reaction was then refluxed until complete saponification was achieved. The ethanol was removed by evaporation and the reaction neutralised with concentrated hydrochloric acid. The white precipitate was collected and washed with water. The material was dried under vacuum to give the title compound (12.19 g)

Workup

  1. temperatureThe reaction was then refluxed until complete saponification
  2. customThe ethanol was removed by evaporation
  3. customthe reaction neutralised with concentrated hydrochloric acid
  4. customThe white precipitate was collected
  5. washwashed with water
  6. customThe material was dried under vacuum

Sources & evidence

ORD record
ord-b0510210807d496687cad289873c9d53
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

Loading…