Triethylamine → 1-Methylcarbamoyl-4-(3',5'-dichlorophenyl) urazole

HRID 371986Notes

Reaction equation

HRID 371986 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[NH:12][NH:11][C:10]2=[O:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.[CH3:23][N:24]=[C:25]=[O:26]>CN(C)C=O.O>[CH3:23][NH:24][C:25]([N:12]1[C:13](=[O:14])[N:9]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)[C:10](=[O:15])[NH:11]1)=[O:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 187550094-(3,5-Dichlorophenyl)-1,2,4-triazolidine-3,5-dione

Product 1

HCID 536345341-Methylcarbamoyl-4-(3',5'-dichlorophenyl) urazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.5 g of 4-(3',5'-dichlorophenyl) urazole in 10 ml of N,N-dimethylformamide were added a drop of triethylamine and, in turn, 0.8 g of methyl isocyanate dropwise at room temperature with agitation. The reaction was continued for one additional hour under the same conditions and the reaction mixture was poured in water to precipitate crystals which were filtered and recrystallized from acetoneethanol to obtain 1-methylcarbamoyl-4-(3',5'-dichlorophenyl) urazole in an amount of 2.1 g (yield being 68%).

Workup

  1. customdropwise at room temperature
  2. customto precipitate crystals which
  3. filtrationwere filtered
  4. customrecrystallized from acetoneethanol

Sources & evidence

ORD record
ord-7e08e28a5ddb45e792dc145ae6ac7e1e
Source dataset
uspto-grants-1978_05
Patent number
US04088767

Reaction notes

Loading…