Hydrazine hydrate (1:1) → 2-Chloro-4,5-bis(4-chlorophenyl)-6-hydrazinylpyrimidine

HRID 271426Notes

Reaction equation

HRID 271426 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:3]=1.O.[NH2:24][NH2:25]>N1C=CC=CC=1.O>[Cl:1][C:2]1[N:3]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[C:6]([NH:24][NH2:25])[N:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 598347942,4-Dichloro-5,6-bis(4-chlorophenyl)pyrimidine

Product 1

HCID 587728472-Chloro-4,5-bis(4-chlorophenyl)-6-hydrazinylpyrimidineYield 95.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2,4-Dichloro-5,6-bis(4-chlorophenyl)pyrimidine (1.8 g, 4.86 mmol) was dissolved in pyridine (5 mL) and hydrazine monohydrate (0.26 mL, 5.36 mmol) was added. The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was then diluted with water (10 mL) and extracted with EtOAc (10 mL×2). The combined organic extracts were washed with water, followed by saturated aqueous NaCl, dried (MgSO4), and concentrated at reduced pressure to obtain 1.7 g of the title compound, as a mixture with its regioisomer, as a yellow solid. HPLC/MS: title compound retention time=3.261 min, [M+H]30 =365; regioisomer retention time 3.385 min.

Workup

  1. extractionextracted with EtOAc (10 mL×2)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-85d627069afe4dcca3a4f3cda3034ab7
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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