Potassium Hydroxide → HCID 178487784, compound

HRID 321959Notes

Reaction equation

HRID 321959 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3)[NH:8][C:4]=2[C:3]=1[CH2:23][C:24]([O:26]CC)=[O:25].[OH-].[K+]>C(O)C>[F:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([O:19][CH3:20])[C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=3)[NH:8][C:4]=2[C:3]=1[CH2:23][C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178470729HCID 178470729, compound

Product 1

HCID 178487784HCID 178487784, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-[5-Fluoro-2-(3,4,5-trimethoxyphenyl)benzimidazolyl]acetate (11.99 mmole, 4.65 g) and potassium hydroxide (40 mmole, 2.24 g) in ethanol (80 ml) is stirred at reflux for 2 hours. The solvent is evaporated and the residue is charged with water (100 ml) and ether (100 ml). The aqueous layer is washed with ether (2×50 ml) and charged with concentrated HCl (pH 1). After 24 hours the colorless precipitate is filtered off and dried in vacuo (R1=(CH2)x—C(O)—OR4, x=1, R2=3,4,5-trimethoxyphenyl, R3=F, R4=hydrogen, n=1).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent is evaporated
  3. additionthe residue is charged with water (100 ml) and ether (100 ml)
  4. washThe aqueous layer is washed with ether (2×50 ml)
  5. additioncharged with concentrated HCl (pH 1)
  6. filtrationAfter 24 hours the colorless precipitate is filtered off
  7. dry with materialdried in vacuo (R1=(CH2)x—C(O)—OR4, x=1, R2=3,4,5-trimethoxyphenyl, R3=F, R4=hydrogen, n=1)

Sources & evidence

ORD record
ord-4b823b9953814294beb8b1423b77fb12
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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