Pyridine → HCID 20457196, compound

HRID 1262624Notes

Reaction equation

HRID 1262624 reaction equation
[C:1]([NH:4][NH2:5])(=[O:3])[CH3:2].N1C=CC=CC=1.[Br:12][C:13]([Br:18])([Br:17])[C:14](Cl)=[O:15]>C(#N)C>[C:1]([N:4]([C:14](=[O:15])[C:13]([Br:18])([Br:17])[Br:12])[NH2:5])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 14039AcetohydrazideHCID 599146Acetyl chloride, tribromo-

Product 1

HCID 20457196HCID 20457196, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4.68 g (0.063 mol) of acetohydrazide (2-a) and 5 g (0.063 mol) of pyridine were dissolved in 50 ml of acetonitrile, and stirred with cooling in an ice-bath. Thereto, a solution of 20 g (0.064 mol) of tribromoacetic acid chloride (which was prepared from tribromoacetic acid and thionyl chloride, and had b.p. of 800°-81° C./17 mm Hg) dissolved in 20 ml of acetonitrile was added dropwise. After the conclusion of the dropwise addition, the stirring ring was further continued for 30 min. Thereupon, a white precipitate was deposited. It was filtered off, and washed with successive, acetonitrile and water. Thus, 10.7 g (0.030 mol) of N-acetyl-N-tribromoacetylhydrazine (3-a) was obtained. Yield 48%.

Workup

  1. temperaturewith cooling in an ice-bath
  2. additionwas added dropwise
  3. additionAfter the conclusion of the dropwise addition
  4. filtrationIt was filtered off
  5. washwashed with successive, acetonitrile and water

Sources & evidence

ORD record
ord-a074555aadd940e982a9c68e6f1f2fa3
Source dataset
uspto-grants-1984_06
Patent number
US04452885

Reaction notes

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