Hydrogen Cyanide → HCID 20570661, compound

HRID 1577478Notes

Reaction equation

HRID 1577478 reaction equation
[CH:1]#[N:2].[CH:3]([O:6][C:7]([C:9]1[CH:10]2[CH:12]([CH2:13][N:14]=1)[CH2:11]2)=[O:8])([CH3:5])[CH3:4]>C(OCC)C.C(Cl)(Cl)Cl>[C:1]([C:9]1([C:7]([O:6][CH:3]([CH3:5])[CH3:4])=[O:8])[NH:14][CH2:13][CH:12]2[CH:10]1[CH2:11]2)#[N:2]

Participants

5

Reactant 2

HCID 768Hydrogen Cyanide2×HCID 20570659HCID 20570659, compound

Product 1

HCID 20570661HCID 20570661, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 6212ChloroformSolvent

Procedure

30 ml of liquid hydrogen cyanide was rapidly added drop-by-drop to a stirred and ice-cooled solution of 2 g of 2-isopropoxycarbonyl-3-azabicyclo[3.1.0]hex-2-ene in 50 ml of dry diethyl ether. The solution was stirred at 0° to 5° C. for 7 hours and then allowed to warm up to room temperature. The diethyl ether and residual hydrogen cyanide were blown off with nitrogen. The residue was taken up in diethyl ether, dried over sodium sulphate and evaporated down. An orange liquid was obtained; it was dissolved in chloroform and passed over an alumina column, eluting with chloroform. After the first 100 ml was collected, the next 300 ml was collected and evaporated down, to give 1 as a straw-colured liquid.

Workup

  1. stirringThe solution was stirred at 0° to 5° C. for 7 hours
  2. dry with materialdried over sodium sulphate
  3. customevaporated down
  4. customAn orange liquid was obtained
  5. washeluting with chloroform
  6. customAfter the first 100 ml was collected
  7. customthe next 300 ml was collected
  8. customevaporated down

Sources & evidence

ORD record
ord-65824ee2921f4b2dbb1206ff1772838b
Source dataset
uspto-grants-1981_09
Patent number
US04288367

Reaction notes

Loading…