Water → HCID 136398817, compound

HRID 1164375Notes

Reaction equation

HRID 1164375 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:8](=[N:10][OH:11])[NH2:9])[NH:5][C:6]=1[Cl:7].C(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>O1CCOCC1>[C:19]([O:11][N:10]=[C:8]([C:4]1[NH:5][C:6]([Cl:7])=[C:2]([Cl:1])[N:3]=1)[NH2:9])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 135971987HCID 135971987, compound

Product 1

HCID 136398817HCID 136398817, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

19.5 g (0.1 mol) of 4,5-dichloro-imidazole-2-carbamide-oxime and 10.1 g (0.1 mol) of triethylamine were dissolved in 150 ml of dioxane. 14.05 g (0.1 mol) of benzoyl chloride were added dropwise to this solution at 15°-20° C. The mixture was stirred for a further 1 hour at room temperature and for 2 hours at 50° C. and was then introduced into 500 ml of water. The crystals which had separated out were filtered off, washed with water and dried. 18 g (60.2% of theory) of 4,5-dichloro-imidazole-2-carbamide-O-benzoyl-oxime were obtained. Melting point: 177°-178° C. (from toluene).

Workup

  1. customThe crystals which had separated out
  2. filtrationwere filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f27335e26066417b9d0abfb9e79235a8
Source dataset
uspto-grants-1983_01
Patent number
US04369186

Reaction notes

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