Dimethylacetamide → Butylamine

HRID 218277Notes

Reaction equation

HRID 218277 reaction equation
C([N:4]([CH:7](C)C)[CH2:5][CH3:6])(C)C.[CH2:10]([NH:14][C:15]1[N:20]=[C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:18]=C(Cl)[N:16]=1)[CH2:11][CH2:12][CH3:13].[CH3:27][C:28](N(C)C)=O>>[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].[CH2:10]([NH:14][C:15]1[N:20]=[C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:18]=[C:7]([NH:4][CH2:5][CH2:6][CH2:27][CH3:28])[N:16]=1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 31374Dimethylacetamide2×HCID 81531DiisopropylethylamineHCID 14045984N~2~,N~4~-Dibutyl-6-chloro-1,3,5-triazine-2,4-diamine

Product 2

HCID 8007ButylamineHCID 108917352,4,6-tris(butylamino)-1,3,5-triazine

Conditions

Temperature
0 °C

Procedure

A solution of 150 millimoles of n-butylamine in 50 ml of dimethylacetamide was prepared and cooled to 0° C. To this solution was added at 0° C. a solution of 250 millimoles of diisopropylethylamine and 50 millimoles of N,N′-dibutyl-6-chloro-[1,3,5]triazine-2,4-diamine in 50 ml of dimethylacetamide, the resulting solution was heated under reflux for 4 hours, then cooled to room temperature, and the solvent was distilled off by an evaporator. The reaction mixture was then isolated and purified by silica gel column chromatography to give N,N′,N″-tributyl-[1,3,5]triazine-2,4,6-triamine as an oily substance. The result of 1H-NMR analysis is shown in FIG. 1.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled to room temperature
  4. distillationthe solvent was distilled off by an evaporator
  5. customThe reaction mixture was then isolated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-957b1d14799a401799e2b8bee0f9ed98
Source dataset
uspto-grants-2012_06
Patent number
US08198387B2

Reaction notes

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