Water → (4-tert-Butyl-1,3-thiazol-2-yl)acetonitrile

HRID 1248813Notes

Reaction equation

HRID 1248813 reaction equation
[OH-].[K+].[C:3]([CH2:5][C:6]([NH2:8])=[S:7])#[N:4].Br[CH2:10][C:11](=O)[C:12]([CH3:15])([CH3:14])[CH3:13].O>C(O)C>[CH3:13][C:12]([C:11]1[N:8]=[C:6]([CH2:5][C:3]#[N:4])[S:7][CH:10]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 21642BromopinacoloneHCID 14162772-Cyanoethanethioamide

Product 1

HCID 2796703(4-tert-Butyl-1,3-thiazol-2-yl)acetonitrileYield 51.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 16.5 g of 85% KOH in 250 ml ethanol was added 25.0 g of 2-cyanothioacetamide. After all of this reagent had dissolved, 44.8 g of bromopinacolone was added dropwise over ca 5 min. The reaction temperature spontaneously climbed to 65° C. and a white solid began to deposit. The mixture was stirred and heated at reflux for 1 hour, cooled, poured into 1000 ml water, and extracted with ether. The extract was washed with brine, dried (MgSO4), and concentrated. Kugelrohr distillation of the residual oil gave 23.3 g of the desired product as a light yellow oil b.p. 90°-95° C. (1 mm Hg).

Workup

  1. dissolutionAfter all of this reagent had dissolved
  2. customspontaneously climbed to 65° C.
  3. temperatureheated
  4. temperatureat reflux for 1 hour
  5. temperaturecooled
  6. extractionextracted with ether
  7. washThe extract was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. distillationKugelrohr distillation of the residual oil

Sources & evidence

ORD record
ord-e9333452fd5c4f1eabb52be436566309
Source dataset
uspto-grants-1986_12
Patent number
US04626543

Reaction notes

Loading…