Water → 1-Ethoxycarbonyl-2-(isopropyl carbamoyl)-4-(3',5'-dichlorophenyl) urazole

HRID 371987Notes

Reaction equation

HRID 371987 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[C:8](=[O:9])[NH:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH:28]([N:31]=[C:32]=[O:33])([CH3:30])[CH3:29].O>CN(C)C=O>[CH2:1]([O:3][C:4]([N:6]1[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[C:8](=[O:9])[N:7]1[C:32](=[O:33])[NH:31][CH:28]([CH3:30])[CH3:29])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 544115751-Ethoxycarbonyl-4-(3',5'-dichlorophenyl) urazole

Product 1

HCID 537216181-Ethoxycarbonyl-2-(isopropyl carbamoyl)-4-(3',5'-dichlorophenyl) urazoleYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.2 g of 1-ethoxycarbonyl-4-(3',5'-dichlorophenyl) urazole in 10 ml of N,N-dimethylformamide were added, in sequence, a drop of triethylamine and 0.85 g of isopropyl isocyanate dropwise at room temperature with agitation. After maintaining the same conditions for one hour, the reaction mixture was mixed with water to precipitate crystals which were filtered and recrystallized from ethanol to obtain 1-ethoxycarbonyl-2-(isopropyl carbamoyl)-4-(3',5'-dichlorophenyl) urazole in an amount of 3.0 g, a yield of 75%.

Workup

  1. customdropwise at room temperature
  2. temperatureAfter maintaining the same conditions for one hour
  3. customto precipitate crystals which
  4. filtrationwere filtered
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c0a217d784c5462db0189eccc214a064
Source dataset
uspto-grants-1978_05
Patent number
US04088767

Reaction notes

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