Dimethylformamide → HCID 15838025, compound

HRID 1599491Notes

Reaction equation

HRID 1599491 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([C:13]1[S:17][C:16]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][CH:14]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CN(C)[CH:25]=[O:26]>>[CH:25]([C:20]1[S:19][C:18]([C:16]2[S:17][C:13]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][CH:15]=2)=[CH:22][CH:21]=1)=[O:26]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 15383559HCID 15383559, compound

Product 1

HCID 15838025HCID 15838025, compoundYield 86%

Conditions

Temperature
60 °C

Procedure

Dimethyl formamide (DMF) (8 ml) was stirred at 0° C. for 10 minutes, POCl3 (1 ml) was added and then stirred for 1 hours. 5-Heptyl-2,2'-bithiophene (0.5 g) dissolved in dimethyl formamide (5 ml) was added and stirred at room temperature for half an hour at room temperature, then the temperature was raised to 60° C. and was further stirred for 4 hours. The reaction solution was then extracted with dichloromethane, neutralized with sodium acetate, washed with water to neutrality, dried, concentrated and separated by silica gel chromatography eluted with ethyl acetate/n-hexane (1/15). Light yellowish oily product (0.86 g, 86%) was obtained.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for half an hour at room temperature
  3. stirringwas further stirred for 4 hours
  4. extractionThe reaction solution was then extracted with dichloromethane
  5. washwashed with water to neutrality
  6. customdried
  7. concentrationconcentrated
  8. customseparated by silica gel chromatography
  9. washeluted with ethyl acetate/n-hexane (1/15)

Sources & evidence

ORD record
ord-2ba796f59ed6417f93bf8a1a20922842
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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