Water → HCID 12965738, compound

HRID 2223823Notes

Reaction equation

HRID 2223823 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH2:4][N:3]=1.C([N:19](C(C)C)CC)(C)C.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1.O>C(#N)C>[Cl:8][C:6]1[N:19]=[C:4]([NH:5][C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[N:3]=[C:2]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7813p-ToluidineHCID 81531DiisopropylethylamineHCID 23033170HCID 23033170, compound

Product 1

HCID 12965738HCID 12965738, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 2.59 g portion of 4,6-dichloro-N-(4-fluorophenyl)-1,3,5-triazine was dissolved in 20 ml of acetonitrile, and 2.09 ml of diisopropylethylamine and 1.18 g of p-toluidine were added thereto and stirred overnight at room temperature. The reaction solution was mixed with water and extracted with ethyl acetate, and the organic layer was washed with 1 M hydrochloric acid and saturated brine and then dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, the thus obtained residue was applied to a silica gel column chromatography and eluted with ethyl acetate:n-hexane (1:9), and then the thus obtained crude product was crystallized from benzene, thereby obtaining 2.74 g of 6-chloro-N-(4-fluorophenyl)-N′-(4-methylphenyl)-1,3,5-triazine-2,4-diamine as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with 1 M hydrochloric acid and saturated brine
  3. customdried
  4. customThe solvent was evaporated under a reduced pressure
  5. washeluted with ethyl acetate:n-hexane (1:9)
  6. customthe thus obtained crude product
  7. customwas crystallized from benzene

Sources & evidence

ORD record
ord-317c2627e09342f5a4ff08eab52bf5a3
Source dataset
uspto-grants-2008_05
Patent number
US07375222B2

Reaction notes

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