Pyridine → HCID 21549051, compound

HRID 1605074Notes

Reaction equation

HRID 1605074 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([OH:13])[C:9]([NH:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:21]([O:23][CH3:24])=[O:22]>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([O:13][C:21]([O:23][CH3:24])=[O:22])[C:9]([NH:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 20349087HCID 20349087, compound

Product 1

HCID 21549051HCID 21549051, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1-(4-chlorophenyl)-1-hydroxy-3-methylurea (10 grams; 0.05 mol) in isopropyl alcohol (40 ml), and pyridine (6 ml) were charged into a glass reaction flask equipped with a mechanical stirrer. Methyl chloroformate (5 ml; 0.06 mol) was added to the flask with stirring, at a temperature of about 10° to 15°C. After the addition was completed the reaction mixture was stirred for an additional one-half hour resulting in the formation of a precipitate. After this time, the reaction mixture was poured onto ice and the precipitate was recovered by filtration and dried. The dried precipitate was then recrystallized from a methyl alcohol-water mixture to yield 1-(4-chlorophenyl)-1-methoxycarbonyloxy-3-methylurea having a melting point of 145° to 146°C and having the following elemental analysis as calculated for C10H11ClN2O4 :

Workup

  1. customequipped with a mechanical stirrer
  2. additionAfter the addition
  3. stirringwas stirred for an additional one-half hour
  4. customresulting in the formation of a precipitate
  5. additionAfter this time, the reaction mixture was poured onto ice
  6. filtrationthe precipitate was recovered by filtration
  7. customdried
  8. customThe dried precipitate was then recrystallized from a methyl alcohol-water mixture

Sources & evidence

ORD record
ord-879ddb07fc1a4588a3e7cc170c6d3a8e
Source dataset
uspto-grants-1976_04
Patent number
US03948967

Reaction notes

Loading…