Dimethylformamide → HCID 86672918, compound

HRID 540964Notes

Reaction equation

HRID 540964 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([O:14][C:15]1[CH:19]=[CH:18][S:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH-].[Na+].CN([CH:25]=[O:26])C>>[CH:25]([C:16]1[S:17][CH:18]=[CH:19][C:15]=1[O:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:26]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 12118488HCID 12118488, compound

Product 1

HCID 86672918HCID 86672918, compound

Procedure

To the stirred solution of anhydrous DMF (10 mL) at 0° C. in 100 mL three neck flask under Nitrogen atmosphere, POCl3 (0.53 mL, 5.76 mmol) was added dropwise for 5 minutes. After addition, the reaction mixture was stirred at room temperature for 1 hour. Then 3-octyloxythiophene (1.02 g, 4.80 mmol) in 2 mL DMF was added dropwise at 0° C. for 5 minutes. This solution was stirred at 70° C. for 90 minutes and poured it into ice water and then slowly neutralized with 10% NaOH solution (20 mL). The resultant mixture was heated in a steam-bath for 20 min. The aqueous layer was extracted with CHCl3 (3×50 mL), followed by drying over anhydrous Na2SO4. After the removal of solvents, the crude mixture was chromatographed on silica gel (10% ethyl acetate in hexane) to give 3′ as a colourless oil. (1.0 g, 86%). 1H NMR (CDCl3, 300 MHz, ppm): δ 10.01 (s, 1H), 7.62 (d, 1H, 5.4 Hz), 6.84 (d, 1H, 5.4 Hz), 4.15 (t, 2H, 6.6 Hz), 1.76-1.86 (m, 2H), 1.29-1.46 (m, 10H), 0.89 (t, 3H, 6.6 Hz). M/e 240.12.

Workup

  1. additionAfter addition
  2. stirringThis solution was stirred at 70° C. for 90 minutes
  3. extractionThe aqueous layer was extracted with CHCl3 (3×50 mL)
  4. dry with materialby drying over anhydrous Na2SO4
  5. customAfter the removal of solvents
  6. customthe crude mixture was chromatographed on silica gel (10% ethyl acetate in hexane)
  7. customto give 3′ as a colourless oil

Sources & evidence

ORD record
ord-e320f18effef4cf9947a91a960e42224
Source dataset
uspto-grants-2014_10
Patent number
US08871884B2

Reaction notes

Loading…