Acetaldehyde → 2-(tert-Butylamino)propanenitrile

HRID 1762937Notes

Reaction equation

HRID 1762937 reaction equation
S(=O)(O)[O-].[Na+].[CH:6](=O)[CH3:7].[C:9]([NH2:13])([CH3:12])([CH3:11])[CH3:10].[C-:14]#[N:15].[Na+]>O>[C:9]([NH:13][CH:6]([CH3:7])[C:14]#[N:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 6385Tert-ButylamineHCID 8929Sodium CyanideHCID 23665763Sodium Bisulfite

Product 1

HCID 131056592-(tert-Butylamino)propanenitrileYield 58.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 106 g of sodium bisulfite in 250 ml of water is combined with 44 g of acetaldehyde and the mixture is stirred for one hour at 60°-65° C. The mixture is then cooled to room temperature, 73.1 g of tert-butylamine is added dropwise thereto, and the mixture is stirred for 2 hours at room temperature. Then a solution of 150 g of sodium cyanide in 160 ml of water is added to the reaction mixture, and the latter is stirred for another 2 hours and then allowed to stand at room temperature for 16 hours. The mixture is thereafter extracted with diethyl ether, the ether extract is dried over sodium sulfate, the solvent is evaporated under vacuum, and the residue is distilled at 14 torr, thus obtaining 73.5 g of 2-tert-butylaminopropionitrile, bp 61°-63° C. at 14 torr.

Workup

  1. stirringthe mixture is stirred for 2 hours at room temperature
  2. stirringthe latter is stirred for another 2 hours
  3. waitto stand at room temperature for 16 hours
  4. extractionThe mixture is thereafter extracted with diethyl ether
  5. extractionthe ether extract
  6. dry with materialis dried over sodium sulfate
  7. customthe solvent is evaporated under vacuum
  8. distillationthe residue is distilled at 14 torr

Sources & evidence

ORD record
ord-6f8c48574ac049349b141085b87089d2
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

Loading…