2-Chloro-4,6-diphenyl-1,3,5-triazine → 2-Azido-4,6-diphenyl-s-triazine

HRID 372858

Reaction equation

HRID 372858 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[N-]=[N+]=[N-].[Li+]>C(#N)C>[N:20]([C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1)=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineHCID 33557Sodium AzideHCID 88163Lithium azide

Product 1

HCID 6236432-Azido-4,6-diphenyl-s-triazineYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-chloro-4,6-diphenyl-s-triazine (30 g, 0.112 mol), sodium azide (12.86 g, 0.199 mol) and lithium azide (1.24 g, 0.025 mol) in acetonitrile (550 ml) was stirred at room temperature for 11 days. After filtration, the filtrate on evaporation yielded 6.9 g of 2-azido-4,6-diphenyl-s-triazine, mp 115°-117° C. The residue on extraction with hot heptane, followed by crystallization from heptane, gave an additional 20 g quantity having a mp of 114°-116° C bringing the total yield of 2-azido-4,6-diphenyl-s-triazine to 26.9 g (88% yield). The melting point and infrared spectrum were identical with that of an authentic sample.

Workup

  1. filtrationAfter filtration
  2. customthe filtrate on evaporation

Sources & evidence

ORD record
ord-df79ebdcc6664bc6bdcafcd3396ab76f
Source dataset
uspto-grants-1978_05
Patent number
US04092466

Linked notes

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