4,6-dichloro-N,N-diphenyl-1,3,5-triazin-2-amine → HCID 21532962, compound

HRID 1657349Notes

Reaction equation

HRID 1657349 reaction equation
[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[N:13]=[C:12](Cl)[N:11]=[C:10](Cl)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]1([NH:28][C:29]#[N:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na]>CC(C)=O.O>[C:1]1([N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[N:13]=[C:12]([N:28]([C:29]#[N:30])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:11]=[C:10]([N:7]([C:8]#[N:9])[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 276474,6-dichloro-N,N-diphenyl-1,3,5-triazin-2-amineHCID 86733498HCID 86733498, compound

Product 1

HCID 21532962HCID 21532962, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 31.7g (0.10 mole) of a 2-diphenylamino-4,6-dichloro-s-triazine in 325 ml of acetone at room temperature was added dropwise to a solution of 0.20 mole of sodium phenylcyanamide in 100 ml of water over a 30 minute period. After stirring for 1 hour at room temperature, the reaction mixture was heated at reflux overnight. After cooling the reaction mixture was filtered. The residue was washed with water, acetone and dried to give 25.5g of crude product. Recrystallization from 1500 ml of acetonitrile gave 20.9g of pure DPNCT, m.p. 280°-284°.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling the reaction mixture
  4. filtrationwas filtered
  5. washThe residue was washed with water, acetone
  6. customdried

Sources & evidence

ORD record
ord-674772419f4444618c71eb8fffd54b40
Source dataset
uspto-grants-1976_06
Patent number
US03960783

Reaction notes

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