Hydrazine → HCID 67334948, compound

HRID 2102235Notes

Reaction equation

HRID 2102235 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:21][NH2:22]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[NH:22][N:21]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 673355111-(3,5-Dichlorophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one

Product 1

HCID 67334948HCID 67334948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the intermediate from step A (1.13 g, 3.7 mmol) in DMF (20 mL) was added hydrazine (0.37 mL, 4.07 mmol, 35% aqueous solution). After 2 hours the reaction mixture was concentrated in vacuo. The residue was suspended in H2O (20 mL). A white precipitate crashed out. The aqueous layer was extracted with ethyl acetate (2×). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. An off-white solid was obtained. This material was used in the next step without any further purification. 1H NMR (CDCl3, 500 MHz): δ 7.7(d, J=1.8 Hz, 2H), 7.66(d, J=8.4 Hz, 2H), 7.35(s, 1H), 7.03(d, J=8.7 Hz, 2H), 6.8(s, 1H), 3.91(s, 3H). LC-MS: 2.92 min. (M+H)=319.

Workup

  1. concentrationAfter 2 hours the reaction mixture was concentrated in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customAn off-white solid was obtained
  7. customThis material was used in the next step without any further purification
  8. custom2.92 min. (M+H)=319

Sources & evidence

ORD record
ord-6bb7f84e63ab46d19659abd44727d5f2
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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