Hydrochloric Acid → HCID 178439581, compound

HRID 463361Notes

Reaction equation

HRID 463361 reaction equation
[OH2:1].[OH-].[Na+].[C:4]([C:6]([NH:11][C:12]([C:14]1[N:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17])=O)([CH3:10])[CH:7]([CH3:9])[CH3:8])#[N:5].Cl>C(Cl)Cl>[CH:7]([C:6]1([CH3:10])[NH:11][C:12]([C:14]2[N:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[N:5][C:4]1=[O:1])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 135636102-[(1-Cyano-1,2-dimethylpropyl)aminocarbonyl]nicotinic acid

Product 1

HCID 178439581HCID 178439581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 20 mL of water and 8.40 g (0.105 mol) of 50% sodium hydroxide solution is added 7.83 g (0.030 mol) of 2-[(1-cyano-1,2-dimethylpropyl)aminocarbonyl]nicotinic acid. External heating is applied to raise the temperature to 70°-75° C. where it is maintained for five hours. After cooling the reaction mixture to 20°-30° C., 50 mL of methylene chloride is added and the pH is adjusted to 3.0 by the addition of 37% hydrochloric acid. The organic layer is separated and the solvent is removed by distillation to give 6.71 g of solid 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)nicotinic acid which is 90% pure in 77% yields.

Workup

  1. temperatureExternal heating
  2. temperatureto raise the temperature to 70°-75° C. where it
  3. temperatureis maintained for five hours
  4. temperatureAfter cooling the reaction mixture to 20°-30° C.
  5. customThe organic layer is separated
  6. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-b72a927ee7d64700b73caf1efefa60ef
Source dataset
uspto-grants-1985_05
Patent number
US04518780

Reaction notes

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