N-[4-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]-N'-(1-methylethyl)urea → 4-[[4-[(2,6-Dichlorophenyl)methyl]-6-(methylamino)-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 270628Notes

Reaction equation

HRID 270628 reaction equation
NC(NC)NC(=O)CC1C(Cl)=CC=CC=1Cl.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]2[N:31]=[C:30]([CH2:32][C:33]3[C:38]([Cl:39])=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:40])[N:29]=[C:28]([NH:41][C:42](NC(C)C)=O)[N:27]=2)=[CH:21][CH:20]=1)#[N:18]>CN(C=O)C>[Cl:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:40])[C:33]=1[CH2:32][C:30]1[N:29]=[C:28]([NH:41][CH3:42])[N:27]=[C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:17]#[N:18])=[CH:24][CH:23]=2)[N:31]=1

Participants

4

Reactant 2

HCID 22281695N-[4-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]-N'-(1-methylethyl)ureaHCID 22281696N-[amino(methylamino)methyl]-2,6-dichloro-benzeneacetamide

Product 1

HCID 4864244-[[4-[(2,6-Dichlorophenyl)methyl]-6-(methylamino)-1,3,5-triazin-2-yl]amino]benzonitrileYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
104 °C

Procedure

A mixture of N-[amino(methylamino)methyl]-2,6-dichloro-benzeneacetamide (4.15 g) and intermediate 6 (3.05 g) in DMF (25 ml) was stirred and refluxed for 20 hours. The solvent was evaporated, the residue dissolved in DMF (25 ml) and heated at 80° C. for 16 hours and at 100-108° C. for another 66 hours. The reaction mixture was cooled, quenched with water, extracted with diethyl ether, and washed with dilute NaOH, water, brine, and dried over K2CO3. The solvent was evaporated, and the residue was purified by flash column chromatography, and recrystallized from 2-propanol, and finally from methanol, yielding 0.78 g (12.6%) of 4-[[4-[(2,6-dichlorophenyl)methyl]-6-(methyl-amino)-1,3,5-triazin-2-yl]amino]benzonitrile (compound 7, mp. 229-230° C.).

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in DMF (25 ml)
  4. temperatureThe reaction mixture was cooled
  5. customquenched with water
  6. extractionextracted with diethyl ether
  7. washwashed with dilute NaOH, water, brine
  8. dry with materialdried over K2CO3
  9. customThe solvent was evaporated
  10. customthe residue was purified by flash column chromatography
  11. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-fec64290661f462e8c16d46c11d4b55f
Source dataset
uspto-grants-2008_11
Patent number
US07449575B2

Reaction notes

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