Acetone → HCID 13194680, compound

HRID 464436Notes

Reaction equation

HRID 464436 reaction equation
[CH3:1][O:2][C:3]([NH:5][N:6]=[C:7]([CH3:9])[CH3:8])=[O:4].C(N(CC)CC)C.CC(C)=O.[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>O.C1C=CC=CC=1>[Br:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]=[C:7]([CH3:9])[CH3:8])=[O:27])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 9095211-Methoxycarbonyl-2-isopropylidene hydrazine

Product 1

HCID 13194680HCID 13194680, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

6.5 g of 1-methoxycarbonyl-2-isopropylidene hydrazine (prepared from methoxycarbonyl hydrazine and acetone), 5.3 g of triethylamine and 100 ml of acetone were placed in a 200 ml round-bottom flask, and while stirring with ice-water cooling, 11.0 g of p-bromobenzoyl chloride was added dropwise. Thereafter, the resulting mixture was stirred at room temperature for one hour to complete the reaction. The reaction mixture was added with 50 ml each of benzene and water. The separated organic layer was taken out by fractionation, dried with anhydrous sodium carbonate and then distilled to remove the solvent. The white crystalline mass thus obtained was recrystallized from a mixed solvent of hexane/acetone to yield 13.6 g (87%) of 1-p-bromobenzoyl-1-methoxycarbonyl-2-isopropylidene hydrazine as white crystals having a melting point of 103°-104° C.

Workup

  1. additionwas added dropwise
  2. customthe reaction
  3. dry with materialdried with anhydrous sodium carbonate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe white crystalline mass thus obtained
  7. customwas recrystallized from a mixed solvent of hexane/acetone

Sources & evidence

ORD record
ord-3bcd9aee79e04e45b54848201a7bf2ff
Source dataset
uspto-grants-1985_10
Patent number
US04547524

Reaction notes

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