Water → HCID 19010353, compound

HRID 1741625Notes

Reaction equation

HRID 1741625 reaction equation
C([N:9]1[C:13](=[O:14])[C:12]([CH:16]([CH3:18])[CH3:17])([CH3:15])[N:11]=[C:10]1[C:19]1[N:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][C:20]=1[C:21](OC)=[O:22])(=O)C1C=CC=CC=1.[C-:31]#[N:32].[Na+].[OH2:34]>C(O)C>[C:31]([CH2:29][C:26]1[CH:27]=[N:28][C:19]([C:10]2[NH:9][C:13](=[O:14])[C:12]([CH:16]([CH3:17])[CH3:18])([CH3:15])[N:11]=2)=[C:20]([CH:25]=1)[C:21]([OH:22])=[O:34])#[N:32]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 15676627HCID 15676627, compound

Product 1

HCID 19010353HCID 19010353, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.0 g of 2-(1-benzoyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-bromomethyl-nicotinic acid, methyl ester, in 60 mL ethanol is added 0.24 g sodium cyanide, followed by 10 cc water. The resulting solution is stirred at room temperature for 24 hours and concentrated in vacuo. The residue is partitioned between methylene chloride and water. The aqueous phase is acidified to pH 3 and extracted with methylene chloride, and the combined organic phases are dried and concentrated in vacuo. Chromatography of the residue on silica gel using methylene chloride-methanol mixtures affords the desired product, mp 196°-200° (dec).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is partitioned between methylene chloride and water
  3. extractionextracted with methylene chloride
  4. customthe combined organic phases are dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61c0b9bd286b473a9f0ff18d340de8a0
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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