Cyanogen Bromide → HCID 21285453, compound

HRID 2231633Notes

Reaction equation

HRID 2231633 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Na].[N:19]#[C:20]Br>>[CH3:14][C:12]1[CH:11]=[C:10]([CH3:15])[N:9]=[C:8]([N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20]#[N:19])[N:13]=1

Participants

5

Reactant 4

HCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 91650PyrimethanilHCID 5360545Sodium

Product 1

HCID 21285453HCID 21285453, compound

Procedure

2-Anilino-4,6-dimethylpyrimidine (3.98 g) was treated with sodium hydride in a similar manner to that described in Example 8. The resulting sodium salt was then treated with cyanogen bromide (2.12 g) and the mixture heated under reflux for 4 hours. The mixture was then filtered through silica gel and eluted with dichloromethane and the solution evaporated. The residue was recrystallised from ethyl acetate to give N-(4,6-dimethylpyrimidin-2-yl)-N-phenylcyanamide, m.p. 153°-4°. (Compound 94).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe mixture was then filtered through silica gel
  4. washeluted with dichloromethane
  5. customthe solution evaporated
  6. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-6d04e74edd7a49f6845f6066005007d2
Source dataset
uspto-grants-1988_11
Patent number
US04783459

Reaction notes

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