P-Phenylenediamine → HCID 58577254, compound

HRID 1429910Notes

Reaction equation

HRID 1429910 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-87b8a96980ce4bfe8809579db149810d
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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