Sodium Hydroxide → HCID 178525502, compound

HRID 223663Notes

Reaction equation

HRID 223663 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]1[NH:14][CH2:13][CH2:12][N:11]1[O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]1[NH:14][CH2:13][CH2:12][N:11]1[O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178471737HCID 178471737, compound

Product 1

HCID 178525502HCID 178525502, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.80 g. of ethyl 4-{[2-[(2,6-dichlorophenyl)imino]-1-imidazolidinyl]oxy}butyrate are dissolved in 100 ml. of ethanol, 26.6 ml. of 1 N caustic soda solution are added at room temperature and the mixture is left to stand overnight. The solution is then neutralized with 26.6 ml. of 1 N hydrochloric acid and evaporated in vacuo. The dried residue is digested with a hot 1:1:1 mixture of acetonitrile/ethyl acetate/chloroform. The salt is then filtered off from the solution and the filtrate is evaporated in vacuo. The residue is recrystallized from hot acetonitrile, whereupon 4-{[2-[(2,6-dichlorophenyl)imino]-1-imidazolidinyl]oxy}-butyric acid, m.p. 115°-116° (from acetonitrile) is obtained.

Workup

  1. waitthe mixture is left
  2. customof 1 N hydrochloric acid and evaporated in vacuo
  3. additionThe dried residue is digested with a hot 1:1:1 mixture of acetonitrile/ethyl acetate/chloroform
  4. filtrationThe salt is then filtered off from the solution
  5. customthe filtrate is evaporated in vacuo
  6. customThe residue is recrystallized from hot acetonitrile, whereupon 4-{[2-[(2,6-dichlorophenyl)imino]-1-imidazolidinyl]oxy}-butyric acid
  7. customm.p. 115°-116° (from acetonitrile) is obtained

Sources & evidence

ORD record
ord-b4b06ccf59bf44388366a2cd016aac0e
Source dataset
uspto-grants-1982_10
Patent number
US04355033

Reaction notes

Loading…