Hydrazine → HCID 178503374, compound

HRID 271056Notes

Reaction equation

HRID 271056 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:11](Cl)=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=1)=O.[NH2:19][NH2:20]>C(O)C.C(OCC)(=O)C.O1CCCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:10]2[C:11](=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=2)[NH:20][N:19]=1

Participants

8

Reactant 2

HCID 9321HydrazineHCID 59834315HCID 59834315, compound

Product 1

HCID 178503374HCID 178503374, compound

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-chlorophenyl)-(4-chloro-2-methylsulfanylpyrimidin-5-yl)-methanone (5.3 g, 17.72 mmol) in ethanol (25 mL) was added anhydrous hydrazine (1.12 ml, 2 eq) dropwise with stirring. The reaction was then stirred for 20 minutes, after which it was cooled in an ice bath and the precipitated solid was removed by filtration. The solid was rinsed with cold ethanol. The filtrate was concentrated to provide a crude oil, which was diluted with ethyl acetate (80 mL), tetrahydrofuran (10 mL), methanol (5 mL), and water (80 mL). This mixture was partitioned and the layers separated. The organic layer was collected and dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow powder (2.81 g, (M+H)+=277).

Workup

  1. stirringThe reaction was then stirred for 20 minutes
  2. temperatureafter which it was cooled in an ice bath
  3. customthe precipitated solid was removed by filtration
  4. washThe solid was rinsed with cold ethanol
  5. concentrationThe filtrate was concentrated
  6. customto provide a crude oil, which
  7. customThis mixture was partitioned
  8. customthe layers separated
  9. customThe organic layer was collected
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-da84e21121e14a31b66612ae98c02796
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Reaction notes

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