Hydrazine → HCID 69195118, compound

HRID 1370253Notes

Reaction equation

HRID 1370253 reaction equation
[NH2:1][NH2:2].[C:3]([C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC(N(C(C)C)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:3]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:1][NH2:2])=[O:16])=[CH:13][CH:12]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 129121414-Benzoylbenzoyl chloride

Product 1

HCID 69195118HCID 69195118, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

) A solution of hydrazine (0.023 mol) and N,N-dimethyl-4-pyridinamine (catalytic quantity) in CH2Cl2 (50 ml) was cooled in an ice-water bath. Half of a solution of 4-benzoylbenzoyl chloride (0.023 mol) in CH2Cl2 (60 ml) was added dropwise. The other half of this solution, and a solution of N,N-bis(1-methylethyl)ethanamine (0.023 mol) in CH2Cl2 (40 ml) were added simultaneously and dropwise. The resulting reaction mixture was stirred for 5 hours at RT. The crude reaction mixture was filtered and the filtrate was washed with water and extracted. The separated organic layer was dried (Na2SO4), filtered and the solvent was evaporated, yielding 1.9 g (34%) of 4-benzoylbenzoic acid hydrazide (interm. 12)

Workup

  1. customThe resulting reaction mixture
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. washthe filtrate was washed with water
  5. extractionextracted
  6. dry with materialThe separated organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-809e43a825444f6b803eae627efa6130
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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