Tetralin → 1-(2,4,6-Trichloroanilino)-5-cyano-2,4-pyrimidinedione

HRID 648159Notes

Reaction equation

HRID 648159 reaction equation
C1C2C(=CC=CC=2)CCC1.[C:11]([C:13](=[CH:22][NH:23][NH:24][C:25]1[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=1[Cl:33])[C:14]([NH:16][C:17](OCC)=[O:18])=[O:15])#[N:12]>>[Cl:33][C:26]1[CH:27]=[C:28]([Cl:32])[CH:29]=[C:30]([Cl:31])[C:25]=1[NH:24][N:23]1[CH:22]=[C:13]([C:11]#[N:12])[C:14](=[O:15])[NH:16][C:17]1=[O:18]

Participants

3

Reactant 2

HCID 8404TetralinHCID 70512904alpha-cyano-beta-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide

Product 1

HCID 132322481-(2,4,6-Trichloroanilino)-5-cyano-2,4-pyrimidinedione

Procedure

To 7 ml of tetralin is added 1.5 g of α-cyano-β-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide, and this mixture is heated to 180°-200° under nitrogen for 30 minutes. After cooling, the resulting solid is filtered, washed with pentane, slurried with acetone/hexane and again filtered to give 1-(2,4,6-trichloroanilino)-5-cyano-2,4-pyrimidinedione, m.p.>320°.

Workup

  1. temperaturethis mixture is heated to 180°-200° under nitrogen for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe resulting solid is filtered
  4. washwashed with pentane
  5. filtrationagain filtered

Sources & evidence

ORD record
ord-198c11fb661e4225975621a2900b65d3
Source dataset
uspto-grants-1983_10
Patent number
US04411839

Reaction notes

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