HCID 70495627, compound → HCID 70495676, compound

HRID 1909828Notes

Reaction equation

HRID 1909828 reaction equation
[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]([NH2:20])=O)[S:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>O=P(Cl)(Cl)Cl>[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]#[N:20])[S:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 1

HCID 70495627HCID 70495627, compound

Product 1

HCID 70495676HCID 70495676, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent2×

Procedure

4-Dodecyl-thiophene-2-carboxylic acid amide 2 (5.0 g, 16.9 mmol) was mixed with 50 mL of POCl3 and the mixture was heated at reflux temperature for 2 hours before POCl3 was removed by a rotary evaporator. Dichloromethane (100 mL) was added followed by drop-wise addition of ice water (100 mL). The organic layer was washed with 30 mL of water twice before the solvent was removed. The brown oil obtained was purified with a column of silica gel with hexane/dichloromethane (v/v: 1/1) as the eluent. After removal of the solvent, the product was obtained as a yellow oil (2.49 g, 53% yield).

Workup

  1. temperaturethe mixture was heated
  2. customwas removed by a rotary evaporator
  3. additionDichloromethane (100 mL) was added
  4. additionfollowed by drop-wise addition of ice water (100 mL)
  5. washThe organic layer was washed with 30 mL of water twice before the solvent
  6. customwas removed
  7. customThe brown oil obtained
  8. customwas purified with a column of silica gel with hexane/dichloromethane (v/v: 1/1) as the eluent
  9. customAfter removal of the solvent

Sources & evidence

ORD record
ord-d7d28ec21593461dae9638cc9fbf7f63
Source dataset
uspto-grants-2013_12
Patent number
US08598450B2

Reaction notes

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