Sodium Cyanide → HCID 15293162, compound

HRID 260270Notes

Reaction equation

HRID 260270 reaction equation
Br[CH2:2][C:3]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:6]=2[O:5][C:4]=1[C:15]1[CH:29]=[CH:28][C:18]([CH2:19][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])=[CH:17][CH:16]=1.[C-:30]#[N:31].[Na+]>C(O)C.O>[Cl:14][C:11]1[CH:12]=[CH:13][C:6]2[O:5][C:4]([C:15]3[CH:29]=[CH:28][C:18]([CH2:19][P:20](=[O:27])([O:21][CH2:22][CH3:23])[O:24][CH2:25][CH3:26])=[CH:17][CH:16]=3)=[C:3]([CH2:2][C:30]#[N:31])[C:8](=[O:9])[C:7]=2[CH:10]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 15293167HCID 15293167, compound

Product 1

HCID 15293162HCID 15293162, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A 2.0 g quantity of the compound obtained in Example 23 was dissolved in a mixture of 5 ml of ethanol and 0.6 ml of water. After addition of 0.48 g of sodium cyanide with stirring at room temperature, the reaction mixture was refluxed with heating for 12 hours. After addition of 20 ml of water, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed serially with 20 ml of water and 20 ml of brine and dried over Glauber's salt. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography (eluent: chloroform:ethyl acetate=1:1). The resulting crude crystals were recrystallized from dichloromethane-n-hexane to provide 1.0 g of the title compound as colorless crystals. Table 1 shows the structure and physical property of the compound obtained.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperaturewith heating for 12 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed serially with 20 ml of water and 20 ml of brine
  5. dry with materialdried over Glauber's salt
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe resulting crude crystals were recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-5f9a2b5ced2344a882d324add975e7d3
Source dataset
uspto-grants-1996_06
Patent number
US05527786

Reaction notes

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