Hydrazine → HCID 69195118, compound

HRID 2219084Notes

Reaction equation

HRID 2219084 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-9c554d6bf0224beeb4ed60ea91a1593b
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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