Ethanol → HCID 14953067, compound

HRID 893366Notes

Reaction equation

HRID 893366 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[CH2:19]CC#N)=[CH:4][CH:3]=1.[CH2:27]([OH:29])[CH3:28].[OH-:30].[Na+]>O>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[CH2:19][CH2:28][C:27]([OH:30])=[O:29])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14953066HCID 14953066, compound

Product 1

HCID 14953067HCID 14953067, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3 g of 5-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]-4,4-dimethylvaleronitrile, prepared in Example 157, are dissolved in a mixture composed of 30 ml of water and 30 ml of ethanol. 3 g of sodium hydroxide pellets are added and the mixture is refluxed for 15 hours. After cooling, 100 ml of water are added and the solution obtained is washed with ether. The aqueous phase is acidified by having sulfur dioxide bubbled through it and the crystals obtained are filtered off, washed with water and then with isopropyl ether and dried to give 2.3 g of 5-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]-4,4-dimethylpentanoic acid in the form of crystals melting at 184°-6° C.

Workup

  1. dissolutionare dissolved in a mixture
  2. temperaturethe mixture is refluxed for 15 hours
  3. temperatureAfter cooling
  4. customthe solution obtained
  5. washis washed with ether
  6. custombubbled through it
  7. customthe crystals obtained
  8. filtrationare filtered off
  9. washwashed with water
  10. dry with materialwith isopropyl ether and dried

Sources & evidence

ORD record
ord-27857ed9d08d4017b5847dc4bb267a31
Source dataset
uspto-grants-1992_06
Patent number
US05124336

Reaction notes

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