Water → 6-(3-Methoxynaphthalen-2-yl)-1,3,5-triazine-2,4(1H,3H)-diimine

HRID 1583866Notes

Reaction equation

HRID 1583866 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:15]([NH:17][C:18]([NH2:20])=[NH:19])#[N:16].[OH-].[K+].O>COCCO>[NH2:16][C:15]1[N:17]=[C:18]([NH2:20])[N:19]=[C:13]([C:12]2[C:3]([O:2][CH3:1])=[CH:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 133737273-Methoxynaphthalene-2-carbonitrileHCID 178418324HCID 178418324, compound

Product 1

HCID 119710966-(3-Methoxynaphthalen-2-yl)-1,3,5-triazine-2,4(1H,3H)-diimine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 3.24 grams of 2-methoxy-3-naphthonitrile, 2.23 grams of cyanoguanidine and 0.24 gram of KOH was dissolved in 30 ml of methyl cellosolve with heating and the mixture was heated to reflux for 6.5 hours. After the reaction was completed, the reaction solution was was poured into water, the crystals separated out were taken by filtration, and were recrystallized from ethyl alcohol to give 2,4-diamino-6-(2-methoxy-3-naphthyl)-s-triazine, colourless needles, melting point 243° to 244° C., the yield being 4.12 grams.

Workup

  1. temperaturewith heating
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 6.5 hours
  4. customthe crystals separated out
  5. filtrationwere taken by filtration
  6. customwere recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-514aed68da6e412e8ff3f36d28763527
Source dataset
uspto-grants-1985_11
Patent number
US04554275

Reaction notes

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