Sodium Azide → 4-[[4-Azido-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 270637Notes

Reaction equation

HRID 270637 reaction equation
Cl[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.[N-:26]=[N+:27]=[N-:28].[Na+]>CS(C)=O>[N:26]([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:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=2)[N:3]=1)=[N+:27]=[N-:28]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 4864234-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Product 1

HCID 30032064-[[4-Azido-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of intermediate (27) in dimethylsulfoxide was treated with NaN3 in one portion and was stirred at RT for 28 hours. The reaction mixture was poured into ice and then filtered. The precipitate was washed with cold water and was recrystallized from ACN, yielding 0.46 g of 4-[[4-azido-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile (compound 68).

Workup

  1. additionThe reaction mixture was poured into ice
  2. filtrationfiltered
  3. washThe precipitate was washed with cold water
  4. customwas recrystallized from ACN

Sources & evidence

ORD record
ord-41ac0c09578a440583aa46892bedac1a
Source dataset
uspto-grants-2008_11
Patent number
US07449575B2

Reaction notes

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