Pyridine → HCID 21549053, compound

HRID 1605075Notes

Reaction equation

HRID 1605075 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([OH:15])[C:10]([N:12]([CH3:14])[CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([O:15][C:23]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])[C:10]([N:12]([CH3:13])[CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 21549072HCID 21549072, compound

Product 1

HCID 21549053HCID 21549053, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1-(3,4-dichlorophenyl)-1-hydroxy-3,3-dimethylurea (12.5 grams; 0.05 mol) in isopropyl alcohol (40 ml), and pyridine (6 ml) are charged into a glass reaction flask equipped with a mechanical stirrer. Phenyl chloroformate (7.8 grams; 0.05 mol) is added to the flask, with stirring, at a temperature of about 10° to 15°C. After the addition is completed, the reaction mixture is stirred for an additional period of about one-half hour resulting in the formation of a precipitate. After this time, the reaction mixture is poured onto ice and the precipitate is recovered by filtration and is dried. The dried precipitate is recrystallized to yield 1-(3,4-dichlorophenyl)-1-phenoxycarbonyloxy-3,3-dimethylurea.

Workup

  1. customequipped with a mechanical stirrer
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred for an additional period of about one-half hour
  4. customresulting in the formation of a precipitate
  5. additionAfter this time, the reaction mixture is poured onto ice
  6. filtrationthe precipitate is recovered by filtration
  7. customis dried
  8. customThe dried precipitate is recrystallized

Sources & evidence

ORD record
ord-fa449b650d0a4aed92a4ccd8f7f067d9
Source dataset
uspto-grants-1976_04
Patent number
US03948967

Reaction notes

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