Ethyl chloroformate → HCID 21549056, compound

HRID 1605073Notes

Reaction equation

HRID 1605073 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9]([OH:14])[C:10]([NH:12][CH3:13])=[O:11].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9]([O:14][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]([NH:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 21549058HCID 21549058, compound

Product 1

HCID 21549056HCID 21549056, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(2,5-dichlorophenyl)-1-hydroxy-3-methylurea (22 grams; 0.09 mol) in 2 N sodium hydroxide (50 ml) was charged into a glass reaction flask equipped with a mechanical stirrer. Ethyl chloroformate (9.6 ml; 0.1 mol) was added to the flask at a temperature of about 10° to 15°C. After the addition the reaction mixture was stirred for a period of about one-half hour, during which time a precipitate was formed. The precipitate was recovered by filtration and was recrystallized from isopropyl alcohol to yield 1-(2,5-dichlorophenyl)-1-ethoxycarbonyloxy-3-methylurea having a melting point of 130° to 132°C and having the following elemental analysis as calculated for C11H12Cl2N2O4 :

Workup

  1. customequipped with a mechanical stirrer
  2. additionAfter the addition the reaction mixture
  3. customwas formed
  4. filtrationThe precipitate was recovered by filtration
  5. customwas recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-c83af525a42041c59e033102a46afc7f
Source dataset
uspto-grants-1976_04
Patent number
US03948967

Reaction notes

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