Hydrazine → HCID 178503465, compound

HRID 230168Notes

Reaction equation

HRID 230168 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:17][CH3:18])=[N:14][C:15]=1[Cl:16])=O.C(N(CC)C(C)C)(C)C.[NH2:29][NH2:30]>C1COCC1.C(OCC)(=O)C.O>[Cl:16][C:15]1[N:14]=[C:13]([S:17][CH3:18])[N:12]=[C:11]2[NH:29][N:30]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:10]=12

Participants

7

Reactant 3

HCID 9321Hydrazine2×HCID 81531DiisopropylethylamineHCID 59812853(2-Chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanone

Product 1

HCID 178503465HCID 178503465, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (2-chlorophenyl)-(4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)-methanone (875 mg, 2.62 mmol) and N,N-diisopropyl ethyl amine (0.69 mL, 1.5 eq) in THF (20 mL) at 0° C. was added a solution of hydrazine (83 μL, 1 eq) in THF (20 mL) dropwise with stirring. After addition was complete, the reaction was gradually warmed to room temperature over 2 hours. Analysis by TLC indicated that there was still starting material remaining. Additional 3 mL of a solution of hydrazine (17 μL) in THF (10 mL) was added dropwise to the reaction mixture, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (150 mL) and water (50 mL). The organic layer was separated, washed with water (4×50 mL) and brine (1×50 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound (867 mg, (M+H)+=311).

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. customThe organic layer was separated
  4. washwashed with water (4×50 mL) and brine (1×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-88ade5060ea44671a5e2ecf441d337ed
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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