Sodium Carbonate → 5-Hydroxy-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methyl-nicotinic acid methyl ester

HRID 867829Notes

Reaction equation

HRID 867829 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([O:10]C(=O)C)[C:7]([CH3:14])=[N:6][C:5]=1[C:15](=O)[NH:16][C:17]([C:22](=[O:24])[NH2:23])([CH3:21])[CH:18]([CH3:20])[CH3:19].P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>O=P(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([OH:10])[C:7]([CH3:14])=[N:6][C:5]=1[C:15]1[NH:23][C:22](=[O:24])[C:17]([CH:18]([CH3:20])[CH3:19])([CH3:21])[N:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24819Phosphorus pentachlorideHCID 137994465-Acetoxy-2-(1-carbamoyl-1,2-dimethylpropyl-carbamoyl)-6-methyl-nicotinic acid methyl ester

Product 1

HCID 1363428005-Hydroxy-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methyl-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 47 g (0.129 mol) 5-acetoxy-2-(1-carbamoyl-1,2-dimethylpropyl-carbamoyl)-6-methyl-nicotinic acid methyl ester and 93.8 g phosphorus pentachloride in 470 ml phosphoroxychloride in stirred 12 hours at room temperature. The solution is then hydrolysed with ice and neutralized with sodium carbonate. The product is extracted with ethyl acetate, the extract is then dried across magnesium sulfate and compressed. The crude product is recrystallized from ethyl acetate/isopropyl ester.

Workup

  1. extractionThe product is extracted with ethyl acetate
  2. dry with materialthe extract is then dried across magnesium sulfate
  3. customThe crude product is recrystallized from ethyl acetate/isopropyl ester

Sources & evidence

ORD record
ord-eb684e9f05e8440e9292dcb34f89697d
Source dataset
uspto-grants-1988_10
Patent number
US04776876

Reaction notes

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