Sodium Hydroxide → HCID 178525502, compound

HRID 1981088Notes

Reaction equation

HRID 1981088 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 1N 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 1N hydrochloric acid and evaporated in vacuo. The dried residue is digested with a hot 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 1N hydrochloric acid and evaporated in vacuo
  3. additionThe dried residue is digested with a hot 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-b6862238956447feb8df10e23271faf4
Source dataset
uspto-grants-1985_04
Patent number
US04511720

Reaction notes

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