Dimethylformamide → HCID 54215258, compound

HRID 442799Notes

Reaction equation

HRID 442799 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][CH2:10][CH:11]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:18][C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:4]([CH3:26])[CH:3]=1.[CH3:27][N:28](C)C=O>Cl.O>[C:27]([C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH2:9][CH2:10][CH:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[O:18][C:19]3[C:24]2=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:4]([CH3:26])[CH:3]=1)#[N:28]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 54158943HCID 54158943, compound

Product 1

HCID 54215258HCID 54215258, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of cuprous cyanide (2.7 g, 30.5 mmol) and 1-(4-bromo-2-methylphenyl)-2-(9H-xanthen-9-ylmethyl)ethanone (10 g, 25.4 mmol) in dry dimethylformamide (80 ml) was heated to reflux under an atmosphere of nitrogen. After 24 h, further cuprous cyanide (2 g, 22.3 mmol) was added and reflux continued for another 20 h. The reaction mixture was cooled and a solution of ferric chloride (8.6 g, 52.9 mmol) in aqueous hydrochloric acid (2M, 200 ml) added. The resulting solution was diluted with water (400 ml) and extracted twice with diethyl ether, the combined extracts were washed with water (5×) and a saturated solution of sodium chloride. The organic phase was dried over magnesium sulphate, filtered and evaporated to a yellow oil. Purified on flash silica eluting with hexane-dichloromethane (4:1 then 3:2 then 1:1) to give 1-(4-cyano-2-methylphenyl)-2-(9H-xanthen-9-ylmethyl)ethanone as a yellow oil. Sample crystallised from hexane m.p. 138°-141° C.

Workup

  1. temperatureto reflux under an atmosphere of nitrogen
  2. temperaturereflux
  3. waitcontinued for another 20 h
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted twice with diethyl ether
  6. washthe combined extracts were washed with water (5×)
  7. dry with materialThe organic phase was dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to a yellow oil
  10. customPurified on flash silica eluting with hexane-dichloromethane (4:1

Sources & evidence

ORD record
ord-95113498b5a844f7a6b6b6ebbae5fa4d
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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