Acetic Acid → HCID 14033023, compound

HRID 2414154Notes

Reaction equation

HRID 2414154 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[OH-].[Na+].[Br:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([C:20]([Cl:24])=[C:21]([Cl:23])[Cl:22])[CH:19]=1)[CH2:13][N:14]=[N+:15]=[N-:16].C(O)(=O)C>C(O)C>[NH2:2][C:1]1[N:14]([CH2:13][C:12]2[CH:17]=[C:18]([C:20]([Cl:24])=[C:21]([Cl:23])[Cl:22])[CH:19]=[C:10]([Br:9])[CH:11]=2)[N:15]=[N:16][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 14798Sodium HydroxideHCID 14033022HCID 14033022, compound

Product 1

HCID 14033023HCID 14033023, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a hot (60° C.) solution of cyanoacetamide (546 mg) in 20 ml of ethanol, 6.47 ml of a methanolic solution of NaOH (1N) was added and the resulting mixture was stirred at 60° C. for 20 minutes. A solution of 3-bromo-5-(trichlorovinyl)benzyl azide (1.02 g) in 10 ml of ethanol was added and the reaction mixture heated at 60° C. for two hours. The pH of the solution was adjusted to ~6 with acetic acid and then concentrated to a small volume. Dilution with 50 ml of water afforded a precipitate which was washed thoroughly with water. The precipitate was recrystallized from 8 ml of ethanol to give 466 mg of pure product, m.p. 175°-177° C.

Workup

  1. temperaturethe reaction mixture heated at 60° C. for two hours
  2. concentrationconcentrated to a small volume
  3. customDilution with 50 ml of water afforded a precipitate which
  4. washwas washed thoroughly with water
  5. customThe precipitate was recrystallized from 8 ml of ethanol

Sources & evidence

ORD record
ord-7000ddd8b6f941e6b937155530dac33f
Source dataset
uspto-grants-1988_01
Patent number
US04721791

Reaction notes

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