Hexylamine → N~2~-Hexyl-1,3,5-triazine-2,4,6-triamine

HRID 2163617Notes

Reaction equation

HRID 2163617 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4](Cl)[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16]([NH2:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C)C=O>[CH2:16]([NH:22][C:4]1[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([NH2:8])[N:5]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8102HexylamineHCID 10340Sodium CarbonateHCID 188311,3,5-Triazine-2,4-diamine, 6-chloro-

Product 1

HCID 19734692N~2~-Hexyl-1,3,5-triazine-2,4,6-triamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 72.8 g. (0.500 mole) of 2,4-diamino-6-chloro-s-triazine, 63.6 g. (0.600 mole) of anhydrous sodium carbonate, and 200 ml. of N,N-dimethylformamide (DMF) was heated over 43 minutes of 124° C. To this was added, over a period of 2.35 hours, a solution of 60.7 g. (0.600 mole) of n-hexylamine in 100 ml. of DMF; temperature was controlled at 122°-127° C. during the addition. The reaction mixture was heated for an additional 19 hours at 124°-125° C., then was filtered hot. The filter cake was washed with 100 ml of hot DMF, and the combined filtrate was cooled and added with stirring to about 5 liters of ice-water. The precipitate was recovered by filtration, reslurried with 3 liters of water, filtered again, washed thoroughly with deionized water, and dried to constant weight in a vacuum oven at 60° C. The yield of n-hexylmelamine, m.p. 115°-117.5° C., was 91.4 g. (87.0%).

Workup

  1. additionA mixture of 72.8 g
  2. additionTo this was added, over a period of 2.35 hours
  3. additiontemperature was controlled at 122°-127° C. during the addition
  4. temperatureThe reaction mixture was heated for an additional 19 hours at 124°-125° C.
  5. filtrationwas filtered hot
  6. washThe filter cake was washed with 100 ml of hot DMF
  7. temperaturethe combined filtrate was cooled
  8. additionadded
  9. filtrationThe precipitate was recovered by filtration
  10. filtrationfiltered again
  11. washwashed thoroughly with deionized water
  12. customdried to constant weight in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-6907d8de27b74d2596a39b1ffe679d7e
Source dataset
uspto-grants-1979_01
Patent number
US04136092

Reaction notes

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