Sodium Acetate → HCID 86685827, compound

HRID 1045799Notes

Reaction equation

HRID 1045799 reaction equation
[C:1]([NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=O)(=S)[CH3:2].C([O-])(=O)C.[Na+].Cl.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][NH2:34])=[CH:29][C:28]=1[CH3:35]>O1CCOCC1.C(O)(=O)C>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:5]([CH:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]3)=[N:4][C:1]([CH3:2])=[N:34]2)=[CH:29][C:28]=1[CH3:35]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 18355390(4-Chloro-3-methylphenyl)hydrazine--hydrogen chloride (1/1)HCID 86685826HCID 86685826, compound

Product 1

HCID 86685827HCID 86685827, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

The product from step A (3.09 g, 10.79 mmol), sodium acetate (0.879, 10.7 mmol) and (4-chloro-3-methylphenyl)hydrazine hydrochloride (2.24 g, 11.6 mmol) were mixed in dioxane (25 mL) and acetic acid (25 mL). The reaction mixture was warmed at 90° C. with stirring for 16 h, cooled to rt and the volatiles were removed. Purification of the residue on SiO2 (5 to 60% ethyl acetate, hexanes) afforded the title compound, which was used without further purification. HPLC/MS: 335.0, 337.0 (M-55), Rt=3.40 (LC4).

Workup

  1. temperaturecooled to rt
  2. customthe volatiles were removed
  3. customPurification of the residue on SiO2 (5 to 60% ethyl acetate, hexanes)

Sources & evidence

ORD record
ord-e85fd8e8232445f68c6cbf24875cb38b
Source dataset
uspto-grants-2013_10
Patent number
US08569299B2

Reaction notes

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