(2,6-Dichlorophenyl)hydrazine monohydrochloride → HCID 89388322, compound

HRID 2402953Notes

Reaction equation

HRID 2402953 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[C:15]([C:16]([O:18]CC)=O)=[CH:14][N:13]=[C:12]([S:21][CH3:22])[N:11]=2)=O)[CH:5]=[CH:4][CH:3]=1.Cl.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1[NH:32][NH2:33]>FC(F)(F)CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:10]3[N:11]=[C:12]([S:21][CH3:22])[N:13]=[CH:14][C:15]=3[C:16](=[O:18])[N:32]([C:26]3[C:25]([Cl:24])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:31])[N:33]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723909(2,6-Dichlorophenyl)hydrazine monohydrochlorideHCID 89388354HCID 89388354, compound

Product 1

HCID 89388322HCID 89388322, compound

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Conditions

Temperature
108 °C

Procedure

To a suspension of Example 175A (512 mg, 1.52 mmol) in 2,2,2-trifluoroethanol (15 mL) was added 2,6-dichlorophenylhydrazine hydrochloride (324 mg, 1.516 mmol). The mixture was heated in a sealed tube at 108° C. overnight. After cooling, the mixture was partitioned between ethyl acetate and brine. The organic phase was concentrated. The residue was separated by flash chromatography (15-50% gradient ethyl acetate in hexane) to provide the title compound. MS (DCI/NH3) m/z 451 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between ethyl acetate and brine
  3. concentrationThe organic phase was concentrated
  4. customThe residue was separated by flash chromatography (15-50% gradient ethyl acetate in hexane)

Sources & evidence

ORD record
ord-53980790ef314e6d98ad146c87120f27
Source dataset
uspto-grants-2014_08
Patent number
US08796289B2

Reaction notes

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