Hydrochloric Acid → HCID 11393032, compound

HRID 2358298Notes

Reaction equation

HRID 2358298 reaction equation
[CH:1]1([N:4]2[C:13]([C:14]#[N:15])=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:23]C)[CH:10]=3)[C:5]2=[O:25])[CH2:3][CH2:2]1.[C-]#N.[Na+].Cl>CS(C)=O.O>[CH:1]1([N:4]2[C:13]([C:14]#[N:15])=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:23])[CH:10]=3)[C:5]2=[O:25])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 11371041HCID 11371041, compound

Product 1

HCID 11393032HCID 11393032, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of the methyl ether 61 (3 g, 9 mmol) and NaCN (3.5 g, 72 mmol) in DMSO was heated at 160° C. for 3 h. The mixture was cooled, diluted with water, acidified with concentrated HCl and then extracted with EtOAc. The combined organic extracts were basified with 1N NaOH and washed with EtOAc. The aqueous layer was acidified with concentrated HCl and then extracted with EtOAc. Drying with Na2SO4 and concentration in vacuo gave a residue was purified by crystallization from EtOAc/hexanes.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialDrying with Na2SO4 and concentration in vacuo
  6. customgave a residue
  7. customwas purified by crystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-a0ab7f3d2b61440a906bbcc4388515a7
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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