Aniline → HCID 12690396, compound

HRID 1005910Notes

Reaction equation

HRID 1005910 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1CCCC1=O.C(OCC)(=O)C>[Cl-].[Na+].O>[NH:9]([C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 709434,6-Dichloropyrimidine

Product 1

HCID 12690396HCID 12690396, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

4,6-Dichloropyrimidine (1 g) and aniline (746 mg) were added to N-methylpyrolidin-2-one (20 mL) and stirred at 120° C. for 24 hours. The resultant mixture was cooled to room temperature, to which ethyl acetate (30 mL) and brine (30 mL) were added, and stirred for 30 minutes. An organic layer was separated, dried (MgSO4), filtered and then concentrated under reduced pressure. The title compound (950 mg) was obtained by silica gel column chromatography (ethyl acetate/n-hexane=1/5).

Workup

  1. additionwere added
  2. stirringstirred for 30 minutes
  3. customAn organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26a8a21008244cea96e475bacea80245
Source dataset
uspto-grants-2004_09
Patent number
US06787551B2

Reaction notes

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