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

HRID 270627

Reaction equation

HRID 270627 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])[N:5]=[C:4]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:3]=1.[H-].[Na+].[N:28]([CH:31]([CH3:33])[CH3:32])=[C:29]=[O:30]>CN(C=O)C>[C:22]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:4]2[N:5]=[C:6]([CH2:8][C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[N:7]=[C:2]([NH:1][C:29]([NH:28][CH:31]([CH3:33])[CH3:32])=[O:30])[N:3]=2)=[CH:25][CH:24]=1)#[N:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 61277Isopropyl isocyanateHCID 4863624-[[4-Amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Product 1

HCID 22281695N-[4-[(4-cyanophenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]-N'-(1-methylethyl)ureaYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound (1) (1.0 g) and sodium hydride (0.11 g), in DMF (20 ml) was stirred for 20 minutes at RT under argon flow. Then, 2-isocyanato-propane (0.27 ml) was added dropwise over 30 minutes and the reaction mixture was allowed to stir at RT overnight. The solvent was evaporated and water added. The residue was filtered, washed with water and diethyl ether, and recrystallized from 1,4-dioxane. The precipitate was filtered off and dried, yielding 0.95 g (85.1%) of N-[4-[(4-cyano-phenyl)amino]-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]-N′-(1-methylethyl)-urea (compound 6, mp. 267-268° C.).

Workup

  1. customThe solvent was evaporated
  2. additionwater added
  3. filtrationThe residue was filtered
  4. washwashed with water and diethyl ether
  5. customrecrystallized from 1,4-dioxane
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-4033b7dab6794c12b32749cba7375600
Source dataset
uspto-grants-2008_11
Patent number
US07449575B2

Linked notes

Loading…