Water → HCID 178439583, compound

HRID 1741617Notes

Reaction equation

HRID 1741617 reaction equation
[CH:1]([C:4]1([CH3:20])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N+:18]([O-])=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[N:5]1)([CH3:3])[CH3:2].C(OC(=O)C)(=[O:23])C.N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[OH:23][C:17]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([C:6]2[NH:7][C:8](=[O:9])[C:4]([CH:1]([CH3:3])[CH3:2])([CH3:20])[N:5]=2)[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 53751268HCID 53751268, compound

Product 1

HCID 178439583HCID 178439583, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 3 g of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid -1-oxide, 2.24 g of acetic anhydride, and 0.4 g of pyridine in 80 mL of toluene is stirred and heated at reflux for 3 hours. The reaction mixture is cooled to 10° C. and 75 mL of cold water is added with vigorous stirring. The resulting yellow solid is filtered, washed with toluene, and air dried. Recrystallization of this solid from methanol affords the desired product as a white solid, mp 201°-203° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. filtrationThe resulting yellow solid is filtered
  4. washwashed with toluene, and air
  5. customdried
  6. customRecrystallization of this solid from methanol

Sources & evidence

ORD record
ord-89cdbf3a7a3e492c92caea7c2597a117
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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