Dimethylformamide → HCID 15661018, compound

HRID 1087386Notes

Reaction equation

HRID 1087386 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[CH3:19][N:20](C)C=O>O>[C:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:19]#[N:20])=[CH:11][CH:12]=3)[S:7][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 15661017HCID 15661017, compound

Product 1

HCID 15661018HCID 15661018, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-acetyl-8-bromophenoxathiin (from Example 4, Step 1) (1.73 g, 5.39 mmol) and cuprous cyanide (1.94 g, 21.6 mmol) in N,N-dimethylformamide (DMF, 15 mL) was refluxed for 7 hours. After cooling, the mixture was diluted with water and the precipitated solid filtered. This solid was boiled with ethyl acetate (100 mL) and filtered. The process was repeated with THF (100 mL, then 50 mL) and the combined filtrates evaporated to afford a yellow solid. This was purified by column chromatography on silica gel, eluting with a 1:3 mixture of ethyl acetate-hexane, to afford the title nitrile (774 mg) as a yellow solid, m.p.: 179°-183° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated solid filtered
  4. filtrationfiltered
  5. custom50 mL) and the combined filtrates evaporated
  6. customto afford a yellow solid
  7. customThis was purified by column chromatography on silica gel
  8. washeluting with a 1:3 mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-237472e479004da5a306d66045e850df
Source dataset
uspto-grants-1991_07
Patent number
US05036067

Reaction notes

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