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

HRID 515325Notes

Reaction equation

HRID 515325 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 93.4%

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 (12.1 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-c504d9ca6e2f4b2bb229cc65251b51d4
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…