m-Chloroperbenzoic acid → HCID 178508577, compound

HRID 1156624Notes

Reaction equation

HRID 1156624 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH2:12][C:13]1[N:18]=[C:17]([NH2:19])[N:16]=[C:15]([N:20]2[CH2:25][CH:24]=[CH:23][CH2:22][CH2:21]2)[N:14]=1>C(COC)OC>[NH2:19][C:17]1[N+:18]([O-:9])=[C:13]([NH2:12])[N:14]=[C:15]([N:20]2[CH2:21][CH:22]=[CH:23][CH2:24][CH2:25]2)[N:16]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20535131HCID 20535131, compound

Product 1

HCID 178508577HCID 178508577, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

191 g. of m-chloroperbenzoic acid are dissolved in 800 ml. of dimethoxyethane and cooled to -5° C. 103 g. of 2,4-diamino-6-[3,6-dihydro-1(2H)-pyridyl]-s-triazine are then added in solid form within 2.5 hours. The mixture is left to warm to room temperature and then stirred overnight. The solvent is then concentrated at 20° C. under reduced pressure and 200 ml. of water are added. The pH value is then adjusted to 10 with sodium hydroxide and the solution is continuously extracted with chloroform for 20 hours. The solvent is then evaporated off and the crude product is chromatographed over silica gel, there being obtained pure 2,4-diamino-6-[3,6-dihydro-1(2H)-pyridyl]-s-triazine-3-oxide having a melting point of 261°-265° C. (decomposition).

Workup

  1. waitThe mixture is left
  2. concentrationThe solvent is then concentrated at 20° C. under reduced pressure and 200 ml
  3. additionof water are added
  4. extractionthe solution is continuously extracted with chloroform for 20 hours
  5. customThe solvent is then evaporated off
  6. customthe crude product is chromatographed over silica gel, there

Sources & evidence

ORD record
ord-6a8fae80fd73486086781db42fef9b4f
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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