Sodium Methoxide → 4-Cyclopropyl-6-methoxy-1,3,5-triazin-2-amine

HRID 652228Notes

Reaction equation

HRID 652228 reaction equation
[CH3:1][O-:2].[Na+].[NH2:4][C:5]1[N:10]=[C:9]([CH2:11][CH2:12][CH2:13]Cl)[N:8]=[C:7](C(Cl)(Cl)Cl)[N:6]=1>CO>[CH:11]1([C:9]2[N:10]=[C:5]([NH2:4])[N:6]=[C:7]([O:2][CH3:1])[N:8]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 201996142-Amino-4-(3-chloropropyl)-6-trichloromethyl-1,3,5-triazine

Product 1

HCID 27265914-Cyclopropyl-6-methoxy-1,3,5-triazin-2-amineYield 12.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 10.8 g of sodium methylate in 50 ml of methanol are added 28.9 g of 2-amino-4-(3-chloropropyl)-6-trichloromethyl-1,3,5-triazine, and the mixture is stirred at 60° C. for 80 minutes. The formed suspension is filtered under suction, diluted with 250 ml of water, and extracted 3 times with 200 ml of ethylene chloride each time. The organic phases are dried, filtered, and concentrated by evaporation. The oil which remains in purified through a silica gel column, the eluant is evaporated off to leave 2.1 g of the title product, which is recrystallised from ether/chloroform, m.p. 158°-159° C.

Workup

  1. filtrationThe formed suspension is filtered under suction
  2. additiondiluted with 250 ml of water
  3. extractionextracted 3 times with 200 ml of ethylene chloride each time
  4. customThe organic phases are dried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customin purified through a silica gel column
  8. customthe eluant is evaporated off

Sources & evidence

ORD record
ord-e454ad69cda540239710a39978bafda5
Source dataset
uspto-grants-1987_06
Patent number
US04670559

Reaction notes

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