Methyl Bromide → 1-Methyl-2-acetyl-4-(3',5'-dichlorophenyl) urazole

HRID 371985Notes

Reaction equation

HRID 371985 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=2)[C:4](=[O:5])[NH:3]1.ClC1C=C(N2C(=O)NNC2=O)C=C(Cl)C=1.CBr.[C:34](Cl)(=[O:36])[CH3:35]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][N:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([Cl:16])[CH:12]=[C:13]([Cl:15])[CH:14]=2)[C:4](=[O:5])[N:3]1[C:34](=[O:36])[CH3:35]

Participants

7

Reactant 4

HCID 6323Methyl BromideHCID 6367Acetyl chlorideHCID 187550094-(3,5-Dichlorophenyl)-1,2,4-triazolidine-3,5-dioneHCID 206160181-Methyl-4-(3',5'-dichlorophenyl) urazole

Product 1

HCID 543057671-Methyl-2-acetyl-4-(3',5'-dichlorophenyl) urazoleYield 76.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2.6 g of 1-methyl-4-(3',5'-dichlorophenyl) urazole, which had been prepared by reacting 4-(3',5'-dichlorophenyl) urazole and methyl bromide in an equimolar proportion, and 1.0 g of triethylamine in 10 ml of N,N-dimethylformamide was added 0.8 g of acetyl chloride in small increments at room temperature with agitation. After completing the addition, the reaction was carried out on a water bath for 2 hours with continued agitation. The solvent was removed by distillation into vacuo and the mass was poured in water to precipitate crystals which were recrystallized from ethanol to obtain 2.3 g of 1-methyl-2-acetyl-4-(3',5'-dichlorophenyl) urazole in a yield of 76%.

Workup

  1. additionthe addition
  2. customThe solvent was removed by distillation into vacuo
  3. additionthe mass was poured in water
  4. customto precipitate crystals which
  5. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-25336e9fbe29437e8659d4ffa203a17f
Source dataset
uspto-grants-1978_05
Patent number
US04088767

Reaction notes

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