Pyridine → HCID 85717842, compound

HRID 231761Notes

Reaction equation

HRID 231761 reaction equation
[C:1]([CH2:3][C:4]([OH:7])([CH3:6])[CH3:5])#[N:2].N1C=CC=CC=1.[C:14](Cl)([Cl:16])=[O:15]>ClCCl>[C:1]([CH2:3][C:4]([O:7][C:14]([Cl:16])=[O:15])([CH3:6])[CH3:5])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 45687953-Hydroxy-3-methylbutanenitrile

Product 1

HCID 85717842HCID 85717842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroformic cyanotert. butyl ester is prepared by reacting cyanotert butanol (10 g, 100 mMole) and pyridine (10 g, 125 mmole) in dichloromethane (150 ml) at about -40° C. together with liquid phosgene (-70° C., 40 ml, 600 mMole). The mixture is allowed to warm to room temperature and stirred over night. It is then extracted with ice cold aqueous hydrochloric acid (1N) washed twice with ice water immediately dried by shaking several times with fresh anhydrous sodium sulfate, the aqueous phases and the sodium sulfate are twice reextracted with a small amount of dichloromethane, and the combined organic phases are evaporated under reduced pressure (20° C. bath) to yield the product (17 g, 100% yield).

Workup

  1. customat about -40° C.
  2. extractionIt is then extracted with ice cold aqueous hydrochloric acid (1N)
  3. washwashed twice with ice water
  4. customimmediately dried
  5. stirringby shaking several times with fresh anhydrous sodium sulfate
  6. customthe combined organic phases are evaporated under reduced pressure (20° C. bath)

Sources & evidence

ORD record
ord-d1ebdf15f2cd4351ba1ca0c2fabc0f98
Source dataset
uspto-grants-1989_07
Patent number
US04849408

Reaction notes

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