Dicyandiamide → 6-{3-[(Trifluoromethyl)sulfanyl]phenyl}-1,3,5-triazine-2,4-diamine

HRID 867156

Reaction equation

HRID 867156 reaction equation
[F:1][C:2]([F:13])([F:12])[S:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].[C:14]([N:16]=[C:17]([NH2:19])[NH2:18])#[N:15].[OH-].[K+]>COCCO.O>[NH2:15][C:14]1[N:16]=[C:17]([NH2:19])[N:18]=[C:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([S:3][C:2]([F:12])([F:1])[F:13])[CH:5]=2)[N:8]=1

Participants

6

Reactant 3

HCID 10005DicyandiamideHCID 14797Potassium HydroxideHCID 27778613-((Trifluoromethyl)sulphanyl)benzonitrile

Product 1

HCID 232752286-{3-[(Trifluoromethyl)sulfanyl]phenyl}-1,3,5-triazine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

2.9 g of m-trifluoromethylthiobenzonitrile (b.p. 86°-88° C./40 mm Hg) and 1.4 g of dicyanodiamide are dissolved in 3 ml of methylcellosolve and the mixture is then combined with 0.3 g of caustic potash and refluxed for 5 hours. After cooling, the mixture is diluted with water and extracted with ether, and the extract, after evaporation, is recrystallized from methanol. Melting point of the obtained material: 172°-174° C.; yield: 2.4 g.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. customthe extract, after evaporation
  5. customis recrystallized from methanol
  6. custom172°-174° C.

Sources & evidence

ORD record
ord-c0bfc2db8ea2426e851c86b39d3dc437
Source dataset
uspto-grants-1978_07
Patent number
US04103009

Linked notes

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