Water → HCID 20194682, compound

HRID 653409Notes

Reaction equation

HRID 653409 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([O-])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1.[Na+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][C:12]=2[N+:17]([O-:19])=[O:18])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6066655-Bromo-2-chloropyrimidineHCID 20194681HCID 20194681, compound

Product 1

HCID 20194682HCID 20194682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.94 g of 5-bromo-2-chloropyrimidine and 1.93 g of sodium 4-amino-2-nitrophenolate were dissolved in 20 ml of dimethylformamide, and reacted in the atmosphere of nitrogen gas at 150° C. for 5 hours. After the completion of the reaction, the reaction product was poured into water, and extracted with ethyl acetate. The extract layer was washed with brine and dried over anhydrous sodium sulfate, and purified by silica gel column chromatography, whereby 1.35 g of 4-(5-bromo-2-pyrimidinyl)-3-nitroaniline having a melting point of 165° to 167° C. was obtained.

Workup

  1. customreacted in the atmosphere of nitrogen gas at 150° C. for 5 hours
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. custompurified by silica gel column chromatography, whereby 1.35 g of 4-(5-bromo-2-pyrimidinyl)-3-nitroaniline having a melting point of 165° to 167° C.
  7. customwas obtained

Sources & evidence

ORD record
ord-d33a961edd994159a3fa3463d0dbeb0d
Source dataset
uspto-grants-1987_06
Patent number
US04677111

Reaction notes

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