Diisopropylethylamine → 4-cyano-benzoic acid N'-[2-(3-iodo-phenyl)-acetyl]-hydrazide

HRID 1468164Notes

Reaction equation

HRID 1468164 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[C:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=1)#[N:22]>CN(C)C(=O)C.O>[I:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:30][NH:29][C:27](=[O:28])[C:26]2[CH:25]=[CH:24][C:23]([C:21]#[N:22])=[CH:32][CH:31]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4567324-CyanobenzohydrazideHCID 38702203-Iodophenylacetic acid

Product 1

HCID 675080464-cyano-benzoic acid N'-[2-(3-iodo-phenyl)-acetyl]-hydrazideYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 31374DimethylacetamideSolvent

Procedure

Add 1,1-carbonyldimidazole (0.72 g, 4.40 mmol) to a solution of 3-iodo-phenylacetic acid (1.20 g, 4.6 mmol) in 40 mL of N,N-dimethylacetamide, followed by N,N-diisopropylethylamine (0.79 mL, 4.40 mmol). Stir the mixture at room temperature for 2 h, add 4-cyano-benzoic acid hydrazide (0.64 g (4.0 mmol) and heat the mixture to 60° C. for 2 h. Cool the mixture to room temperature and dilute with H2O causing a solid to precipitate from solution. Collect the precipitate by filtration, wash with H2O and diethyl ether dry. Collect any further material that may crystallize from the filtrate. Extract the filtrate with CH2Cl2 and concentrate the combined organic phase provide a clear liquid. Dilute this mixture with H2O resulting in a third crop of material to precipitate from solution. Collect and combine all solid material to give 1.31 g, 71% yield of 4-cyano-benzoic acid N′-[2-(3-iodo-phenyl)-acetyl]-hydrazide as a powder.

Workup

  1. temperatureheat the mixture to 60° C. for 2 h
  2. temperatureCool the mixture to room temperature
  3. customto precipitate from solution
  4. customCollect the precipitate
  5. filtrationby filtration
  6. washwash with H2O and diethyl ether
  7. customdry
  8. customCollect any further material that
  9. custommay crystallize from the filtrate
  10. extractionExtract the filtrate with CH2Cl2
  11. concentrationconcentrate the combined organic phase
  12. customprovide a clear liquid
  13. customto precipitate from solution
  14. customCollect

Sources & evidence

ORD record
ord-9d01dc485a024e46a765fc6d22592844
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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