Isopropanol → HCID 21549073, compound

HRID 1605072Notes

Reaction equation

HRID 1605072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([OH:14])[C:10]([NH:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C)C.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([O:14][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10]([NH:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 10928Ethyl chloroformateHCID 80430Urea, N-(3,4-dichlorophenyl)-N-hydroxy-N'-methyl-

Product 1

HCID 21549073HCID 21549073, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(3,4-dichlorophenyl)-1-hydroxy-3-methylurea (15 grams; 0.06 mol) is isopropyl alcohol (50 ml), and pyridine (7 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer. Ethyl chloroformate (7 ml; 0.09 mol) was then slowly added, with stirring, at a temperature of 10° to 15°C. After the addition was completed stirring was continued for an additional period of about one-half hour resulting in the formation of a precipitate. After this time, the reaction mixture was poured onto ice and the precipitate recovered by filtration. The precipitate was recrystallized from a benzene-hexane mixture to yield 1-(3,4-dichlorophenyl)-1-ethoxycarbonyloxy-3-methylurea having a melting point of 97°-98°C and having the following elemental analysis as calculated for C11H12Cl2N2O4 :

Workup

  1. additionwere charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. additionAfter the addition
  4. stirringwas completed stirring
  5. waitwas continued for an additional period of about one-half hour
  6. customresulting in the formation of a precipitate
  7. additionAfter this time, the reaction mixture was poured onto ice
  8. filtrationthe precipitate recovered by filtration
  9. customThe precipitate was recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-cd023419143e47018672df7d0e50cf90
Source dataset
uspto-grants-1976_04
Patent number
US03948967

Reaction notes

Loading…