Hydrochloric Acid → HCID 15011248, compound

HRID 555954Notes

Reaction equation

HRID 555954 reaction equation
[CH2:1]([OH:8])[C:2]([NH2:7])([CH2:5][OH:6])[CH2:3][OH:4].[OH-].[K+].[C:11](#[N:14])[CH:12]=[CH2:13].Cl>O1CCOCC1>[NH2:7][C:2]([CH2:5][O:6][CH2:13][CH2:12][C:11]#[N:14])([CH2:3][O:4][CH2:13][CH2:12][C:11]#[N:14])[CH2:1][O:8][CH2:13][CH2:12][C:11]#[N:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6503Tris(hydroxymethyl)aminomethaneHCID 7855AcrylonitrileHCID 14797Potassium Hydroxide

Product 1

HCID 15011248HCID 15011248, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tris(hydroxymethyl)aminomethane (24.2 g, 0.2 mol) was added to a mixture of dioxane (25 ml) and aqueous potassium hydroxide (1.2 g KOH in 3 ml water). Acrylonitrile (40 ml, 0.61 mol) was added dropwise. After 2 h the solution was stood in a cold water bath to moderate any exothermic reaction and stirred for 16 h at RT. The solution was neutralized with dil. HCl and filtered. The oil was dissolved in DCE, dried (MgSO4), filtered and concentrated. The brown oil was purified by chromatography (SiO2, CH2Cl2/MeOH 1% to 4%) to give the title product (26.9 g, 0.096 mol, 48%) as a colourless oil. δH (400 MHz, CDCl3) 3.71 (6H, t, J 6.0), 3.47 (6H, s), 2.63 (6H, t, J 6.0); TLC (CH2Cl2/MeOH 10%) 0.55.

Workup

  1. customany exothermic reaction
  2. filtrationfiltered
  3. dissolutionThe oil was dissolved in DCE
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe brown oil was purified by chromatography (SiO2, CH2Cl2/MeOH 1% to 4%)

Sources & evidence

ORD record
ord-058e71808bed4629957cb313b27745ba
Source dataset
uspto-grants-2011_11
Patent number
US08053564B2

Reaction notes

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