Hydrazine hydrate (1:1) → 2-chloro-5,6-diphenyl-4-hydrazinopyrimidine

HRID 2250332Notes

Reaction equation

HRID 2250332 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.O.[NH2:22][NH2:23]>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:22][NH2:23])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 99720612,4-Dichloro-5,6-diphenylpyrimidine

Product 1

HCID 117793522-chloro-5,6-diphenyl-4-hydrazinopyrimidineYield 32.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dichloro-5,6-diphenylpyrimidine (2.0 g, 6.6 mmol) (synthesized according to the procedure described in example 7) was treated with hydrazine hydrate (0.73 g, 14.6 mmol) in ethanol (10 ml) under stirring for 5 hours at room temperature. The reaction mixture was poured onto ice-water mixture. The solid thus separated was extracted with diethylether. The organic extract was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound (0.64 g, 32.5%).

Workup

  1. additionThe reaction mixture was poured onto ice-water mixture
  2. customThe solid thus separated
  3. extractionwas extracted with diethylether
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d9b7c087c7e4e24b0cc6a626de3bc5e
Source dataset
uspto-grants-2008_01
Patent number
US07317014B2

Reaction notes

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