4-Isopropylaniline → HCID 13121218, compound

HRID 544387Notes

Reaction equation

HRID 544387 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1.[CH:10]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)([CH3:12])[CH3:11]>>[CH:10]([C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[C:7]([CH3:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=2)=[CH:15][CH:14]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 74644-IsopropylanilineHCID 126003894-Chloro-5,6-dimethylpyrimidine

Product 1

HCID 13121218HCID 13121218, compoundYield 23.2%

Procedure

To 3.6 g (0.025 mole) of 4-chloro-5,6-dimethylpyrimidine were added 3.4 g (0.025 mole) of p-isopropylaniline; the mixture was then heated at 100°-150° C. for about 3 minutes. The reaction mixture quickly became a solution and soon produced a precipitate, which was separated and then made alkaline by the addition of 50 ml of a dilute aqueous solution of sodium hydroxide. The mixture was then extracted with ethyl acetate and the extract was washed, in turn, with water and with a saturated aqueous solution of sodium chloride. It was then dried over anhydrous sodium sulphate and then the ethyl acetate was distilled off under reduced pressure, to give crystals, which, on recrystallisation froma 3:1 by volume mixture of benzene and hexane, gave 1.4 g (yield 23%) of the desired product in the form of very fine colourless needles melting at132°-133° C.

Workup

  1. temperaturethe mixture was then heated at 100°-150° C. for about 3 minutes
  2. customsoon produced a precipitate, which
  3. customwas separated
  4. additionby the addition of 50 ml of a dilute aqueous solution of sodium hydroxide
  5. extractionThe mixture was then extracted with ethyl acetate
  6. washthe extract was washed, in turn, with water and with a saturated aqueous solution of sodium chloride
  7. dry with materialIt was then dried over anhydrous sodium sulphate
  8. distillationthe ethyl acetate was distilled off under reduced pressure
  9. customto give crystals, which
  10. customon recrystallisation froma 3:1
  11. additionby volume mixture of benzene and hexane

Sources & evidence

ORD record
ord-74c327fdadc74d80b340c577c8ea9239
Source dataset
uspto-grants-1984_05
Patent number
US04450162

Reaction notes

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