M-Phenylenediamine → N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

HRID 81708

Reaction equation

HRID 81708 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[C:24]1([NH2:31])[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1>C(OCCO)C.C(OCC)(=O)C>[C:9]1([S:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:30][C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([NH2:31])[CH:25]=3)[N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7935M-PhenylenediamineHCID 81531DiisopropylethylamineHCID 219952052-Chloro-4-(phenylthio)pyrimidine

Product 1

HCID 68746426N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamineYield 42%

Reagents, catalysts & solvents 2

HCID 8076Glycol monoethyl etherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 2-chloro-4-(phenylthio)pyrimidine (300 mg, 1.35 mmol) and diisopropylethylamine (0.35 mL, 2.02 mmol) in 2-ethoxyethanol (2 mL), was added 1,3-phenylenediamine (291 mg, 2.70 mmol) in one portion. The whole was heated under reflux for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), washed with water and brine. The organic solution was dried (Na2SO4), concentrated in vacuo. The residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (20:80→0:50) as eluant to give the product (167 mg, 42%).

Workup

  1. temperatureThe whole was heated
  2. temperatureunder reflux for 20 hours
  3. washwashed with water and brine
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-2dec037877b041599ed4cd165660a167
Source dataset
uspto-grants-2014_09
Patent number
US08846704B2

Linked notes

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