4-Chloroaniline → HCID 13121220, compound

HRID 544385Notes

Reaction equation

HRID 544385 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>C(O)C>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:2]2[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 126003894-Chloro-5,6-dimethylpyrimidine

Product 1

HCID 13121220HCID 13121220, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To 4.3 g (0.03 mole) of 4-chloro-5,6-dimethylpyrimidine were added 3.8 g (0.03 mole) of p-chloroaniline and about 10 ml of ethanol; the mixture wasthen heated at 130° C. for about 3 minutes. The reaction mixture quickly became a solution and then the hydrochloride of the desired compound precipitated as the solution was allowed to cool. The crystals thus obtained were separated and ground to a powder and then made alkalineby the addition of a dilute aqueous solution of sodium hydroxide. The insolubles were collected by filtration, washed with water and dried. The resulting crystals were recrystallised from benzene, to give 4.2 g (yield 60%) of the desired Compound No. 25, in the form of colourless needles melting at 170°-173° C.

Workup

  1. customthe hydrochloride of the desired compound precipitated as the solution
  2. temperatureto cool
  3. customThe crystals thus obtained
  4. customwere separated
  5. additionground to a powder and then made alkalineby the addition of a dilute aqueous solution of sodium hydroxide
  6. filtrationThe insolubles were collected by filtration
  7. washwashed with water
  8. customdried
  9. customThe resulting crystals were recrystallised from benzene

Sources & evidence

ORD record
ord-3ae3fc4deb9d4c21b6c2263327f2acc2
Source dataset
uspto-grants-1984_05
Patent number
US04450162

Reaction notes

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