Ammonia → HCID 486407, compound

HRID 1363894Notes

Reaction equation

HRID 1363894 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[N:5]=[C:4]([NH:18][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[N:3]=1.[NH3:27].O1CCOCC1>>[NH2:27][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[N:5]=[C:4]([NH:18][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 505445HCID 505445, compound

Product 1

HCID 486407HCID 486407, compoundYield 61.4%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-[[4-chloro-6-[(2,4,6-trimethylphenyl)amino]-1,3,5-triazin-2-yl]-amino]benzonitrile (*A9c) (0.00137 mol) and NH3 in 1,4-dioxane (0.5 M; 0.00548 mol) was heated in a pressure vessel at 100° C. for 6 days. The solvent was evaporated and the residue was dissolved in CH2Cl2, washed with a saturated aqueous NaHCO3 solution, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 100/0, 99/1 and 98/2). The desired fractions were collected and the solvent was evaporated. The residue was recrystallized from toluene. The precipitate was filtered and dried, yielding 0.29 g (61.4%) of 4-[[4-amino-6-[(2,4,6-trimethylphenyl)amino]-1,3,5-triazin-2-yl]amino]-benzonitrile.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with a saturated aqueous NaHCO3 solution
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 100/0, 99/1 and 98/2)
  8. customThe desired fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was recrystallized from toluene
  11. filtrationThe precipitate was filtered
  12. customdried

Sources & evidence

ORD record
ord-17228dbd612c4459903718e358f1be08
Source dataset
uspto-grants-2011_02
Patent number
US07887845B2

Reaction notes

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