Dimethylformamide → HCID 21882247, compound

HRID 722011Notes

Reaction equation

HRID 722011 reaction equation
[C:1]([C:3]1[C:4]([OH:16])=[C:5]2[C:10](=[C:11](O)[C:12]=1[C:13]#[N:14])[N:9]=[CH:8][CH:7]=[CH:6]2)#[N:2].[CH2:17](Br)[CH2:18][CH2:19][CH3:20].[C:22](=[O:25])([O-])[O-].[K+].[K+].C(O[CH2:32][CH3:33])(=O)C.[CH3:34]N(C=O)C>>[CH2:17]([O:16][C:4]1[C:3]([C:1]#[N:2])=[C:12]([C:13]#[N:14])[C:11]([O:25][CH2:22][CH2:34][CH2:32][CH3:33])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8002Butyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 135839353HCID 135839353, compound

Product 1

HCID 21882247HCID 21882247, compound

Conditions

Temperature
50 °C

Procedure

The dinitrile 3 (1.39 g; 6.58 mmol) in DMF (25 mL) was treated with butyl bromide (2.0 mL; 2.55 g; 19 mmol) followed by freshly dried potassium carbonate (2 g) and then the resulting mixture was stirred at 50° C. overnight. After this time ethyl acetate (200 mL) was added and the whole was poured onto water (200 mL) and shaken. After separating the layers, the aqueous layer was extracted with more ethyl acetate (100 mL) and then the combined organic layers were washed with water (3×250 mL), dried (MgSO4), and evaporated to dryness. The remaining solid was triturated with boiling hexane and filtered to give the dibutyl ether 4 as a pale-brown powder (944 mg; 44%). 1H NMR (CDCl3) δ 1.01 [3H, t, J=7.4 Hz, CH3 (Bu)]; 1.03 [3H, t, J=7.4 Hz, CH3 (Bu)]: 1.53–1.66 [4H, m, CH2 (Bu)]; 1.87–1.96 [4H, m, CH2 (Bu)]; 4.52 (2H, t, J=6.5 Hz, OCH2Pr); 4.66 (2H, t, J=6.7 Hz, OCH2Pr); 7.65 (1H, dd, J=8.5, 4.2 Hz, Ar—H); 8.57 (1H, dd, J=8.5, 1.6 Hz, Ar—H); 9.10 (1H, dd, J=4.2, 1.6 Hz, Ar—H)

Workup

  1. additionthe whole was poured onto water (200 mL)
  2. stirringshaken
  3. customAfter separating the layers
  4. extractionthe aqueous layer was extracted with more ethyl acetate (100 mL)
  5. washthe combined organic layers were washed with water (3×250 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customThe remaining solid was triturated with boiling hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-520a7f5cd5024f93b696501fecc2fa73
Source dataset
uspto-grants-2006_11
Patent number
US07138391B2

Reaction notes

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