Ethanol → 3-Chloro-4-(tetrahydro-pyrimidin-2-on-1-yl)-benzoic acid

HRID 551186Notes

Reaction equation

HRID 551186 reaction equation
[Cl:1][C:2]1[CH:3]=C([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH2:13][NH:12][C:11]1=[O:16])C#N.[OH-:17].[Na+].[CH2:19]([OH:21])[CH3:20]>>[Cl:1][C:2]1[CH:3]=[C:20]([CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][CH2:13][NH:12][C:11]1=[O:16])[C:19]([OH:17])=[O:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 667319453-Chloro-4-(tetrahydro-pyrimidin-2-on-1-yl)-benzonitrile

Product 1

HCID 643195303-Chloro-4-(tetrahydro-pyrimidin-2-on-1-yl)-benzoic acid

Conditions

Temperature
100 °C

Procedure

350 mg (1.49 mmol) 3-chloro-4-(tetrahydro-pyrimidin-2-on-1-yl)-benzonitrile are suspended in 5 ml of ethanol and combined with 2.0 ml of 10-molar aqueous sodium hydroxide solution. The mixture is stirred for one hour at 100° C. and then evaporated down i. vac. The aqueous residue is combined with ice, acidified with acetic acid and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over magnesium sulphate and evaporated down i. vac. The aqueous phase is acidified with 6-molar hydrochloric acid, extracted 5 times with ethyl acetate, the combined organic phases are washed with sat. sodium chloride solution, dried over magnesium sulphate and evaporated down i. vac.

Workup

  1. customevaporated down i
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with water and sat. sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down i
  6. extractionextracted 5 times with ethyl acetate
  7. washthe combined organic phases are washed with sat. sodium chloride solution
  8. dry with materialdried over magnesium sulphate
  9. customevaporated down i

Sources & evidence

ORD record
ord-47d2c55f5be749439347886584f13407
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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