Diethyl Malonate → HCID 178516646, compound

HRID 1294413Notes

Reaction equation

HRID 1294413 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[CH2:10][C:11](=[NH:13])[NH2:12].[Na].[C:15](OCC)(=[O:22])[CH2:16][C:17](OCC)=[O:18]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[CH2:10][C:11]1[N:12]=[C:17]([OH:18])[CH:16]=[C:15]([OH:22])[N:13]=1

Participants

5

Reactant 3

HCID 7761Diethyl Malonate2×HCID 5360545SodiumHCID 12690064(2,6-Dichlorophenyl)ethanimidamide--hydrogen chloride (1/1)

Product 1

HCID 178516646HCID 178516646, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To the stirred solution of 2,6-dichlorobenzeneethanimidamide HCl (1:1), (0.0042 mol) in ethanol (20 ml), a solution of sodium (0.013 mol) in ethanol (10 ml) was added dropwise first and then propanedioic acid, diethyl ester (0.0109 mol) was added. The reaction mixture was stirred and refluxed for 4 hours and then stirred at room temperature overnight After adding another equivalent of propanedioic acid, diethyl ester (stirring and refluxing it overnight), the solvent was evaporated and the residue was dissolved in water and acidified with 1 N HCl. The solid was filtered off, washed with water and dried, yielding 0.87 g (76.4%) of 2-[(2,6-dichloro-phenyl)methyl]-4,6-pyrimidinediol (interm. 8). b) 6-chloro-2-[(2,6-dichloro-phenyl)methyl]-4-pyrimidinamine (interm. 9) was prepared starting from intermediate 8 according to the procedures described in example A1b), A2b) & A2c).

Workup

  1. temperaturerefluxed for 4 hours
  2. stirringstirred at room temperature overnight
  3. customthe solvent was evaporated
  4. dissolutionthe residue was dissolved in water
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-cf3b81af6c1d480e89ab8c72742faacb
Source dataset
uspto-grants-2007_07
Patent number
US07241458B1

Reaction notes

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