2,3,3-Trimethyl-2-butanamine → 2,4,6-Tris(1,1,2,2-tetramethylpropylamino)-s-triazine

HRID 2287155Notes

Reaction equation

HRID 2287155 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:15])([C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:10])[N:5]=[C:4]([NH:16][C:17]([CH3:23])([C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:18])[N:3]=1.[CH3:24][C:25]([NH2:31])([C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:26]>>[CH3:24][C:25]([NH:31][C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:10])([CH3:15])[C:11]([CH3:13])([CH3:14])[CH3:12])[N:5]=[C:4]([NH:16][C:17]([CH3:23])([CH3:18])[C:19]([CH3:22])([CH3:20])[CH3:21])[N:3]=1)([CH3:26])[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 2073592,3,3-Trimethyl-2-butanamineHCID 155725772-Chloro-4,6-di(2,3,3-trimethyl-2-butyl)amino-s-triazine

Product 1

HCID 234594942,4,6-Tris(1,1,2,2-tetramethylpropylamino)-s-triazine

Conditions

Temperature
185 °C

Procedure

3.3 g. (9.6 mmole) of 2-chloro-4,6-di(2,3,3-trimethyl-2-butyl)amino-s-triazine and 3.3 g. (30 mmoles) of 2,3,3-trimethyl-2-butylamine are heated at reflux (oil bath 185° C.) for 21 hours. Thin layer chromatography of a sample of the reaction mixture indicates a mixture of starting material and product in a ratio of 3:7. Heating is terminated and the reaction mixture is treated with excess aqueous NaOH. Filtration affords a 4.9 g. of crude beige product. This is digested with 15 ml. of hot acetone, filtered and 2.6 g. of beige solid collected, m.p. 278° C. dec. Recrystallization of this product from hot ethanol gives the pure product, m.p. 317°-321° C. dec.

Workup

  1. additiona mixture of starting material and product in a ratio of 3:7
  2. temperatureHeating
  3. customis terminated
  4. additionthe reaction mixture is treated with excess aqueous NaOH
  5. filtrationFiltration
  6. customaffords a 4.9 g
  7. filtrationof hot acetone, filtered
  8. customof beige solid collected
  9. customRecrystallization of this product from hot ethanol
  10. customgives the pure product, m.p. 317°-321° C. dec.

Sources & evidence

ORD record
ord-82dfd78493744aaf8e835c4235ed510f
Source dataset
uspto-grants-1981_05
Patent number
US04269832

Reaction notes

Loading…