P-Phenylenediamine → HCID 58577254, compound

HRID 82534Notes

Reaction equation

HRID 82534 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[CH:4][N:3]=1.[C:11]1([NH2:18])[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1>CN1CCCC1=O.O>[N+:8]([C:7]1[C:2]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([NH2:18])=[CH:12][CH:13]=2)=[N:3][CH:4]=[N:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 7814P-PhenylenediamineHCID 249037774-Chloro-5-nitropyrimidine

Product 1

HCID 58577254HCID 58577254, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-chloro-5-nitropyrimidine (380 mg) and benzene-1,4-diamine (257 mg) in N-methylpyrrolidone (5 mL) was stirred overnight at ambient temperature. After this time, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with saturated sodium bicarbonate (50 mL) then brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 3:97 methanol/methylene chloride) to afford N-(5-nitropyrimidin-4-yl)benzene-1,4-diamine (260 mg) as a brown oil.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers were washed with saturated sodium bicarbonate (50 mL)
  3. dry with materialbrine (50 mL), dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by chromatography (silica, methylene chloride to 3:97 methanol/methylene chloride)

Sources & evidence

ORD record
ord-a043012d0163485096bbee0536f4b549
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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