Water → N-(6-chloro-4-methylpyrimidin-2-yl)-2-nitroaniline

HRID 1381477Notes

Reaction equation

HRID 1381477 reaction equation
O[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[N:5]=[C:4]([CH3:18])[CH:3]=1.CN(C)C=O.P(Cl)(Cl)([Cl:26])=O.O>C(Cl)(Cl)Cl>[Cl:26][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[N:5]=[C:4]([CH3:18])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178429396HCID 178429396, compound

Product 1

HCID 14602007N-(6-chloro-4-methylpyrimidin-2-yl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 160 g (0.65 mol) of N-(6-hydroxy-4-methylpyrimidin-2-yl)-o-nitroaniline, 2 ml of N,N-dimethylformamide and 120 ml of phosphorus oxychloride are heated at reflux for 3 hours. After having been cooled, and black slurry is dissolved in chloroform and this solution is added dropwise to 1 l of water. The temperature is maintained at 35° by the addition of ice. After 1 hour the organic phase is separated off and the aqueous phase is washed with chloroform. The two chloroform solutions are together dried and concentrated by evaporation. The black residue is dissolved in hot toluene, filtered and crystallised by the addition of hexane. 104.9 g (61%) of the title compound of formula ##STR16## (compound No. 2.007) are obtained in the form of crystals having a melting point of 175° C.

Workup

  1. temperatureare heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter having been cooled
  4. temperatureThe temperature is maintained at 35° by the addition of ice
  5. customAfter 1 hour the organic phase is separated off
  6. washthe aqueous phase is washed with chloroform
  7. dry with materialThe two chloroform solutions are together dried
  8. concentrationconcentrated by evaporation
  9. dissolutionThe black residue is dissolved in hot toluene
  10. filtrationfiltered
  11. customcrystallised by the addition of hexane
  12. custom2.007) are obtained in the form of crystals

Sources & evidence

ORD record
ord-e5d8a8ed2122406fae13e7e3deddb493
Source dataset
uspto-grants-1989_02
Patent number
US04802909

Reaction notes

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