HCID 70495271, compound → HCID 70496058, compound

HRID 1909831Notes

Reaction equation

HRID 1909831 reaction equation
[CH2:1]([C:12]1[C:16]2[S:17][C:18]([C:20]([NH2:22])=O)=[CH:19][C:15]=2[S:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>O=P(Cl)(Cl)Cl>[CH2:1]([C:12]1[C:16]2[S:17][C:18]([C:20]#[N:22])=[CH:19][C:15]=2[S:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 1

HCID 70495271HCID 70495271, compound

Product 1

HCID 70496058HCID 70496058, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent2×

Procedure

To 6-undecyl-thieno[3,2-b]thiophene-2-carboxylic acid amide (4.2 g) was added 30 mL of POCl3 and the mixture was heated to reflux for 2 hours before POCl3 was removed by a rotary evaporator. Dichloromethane (50 mL) was added and then 100 mL of ice water was added dropwise. The organic layer was further washed with 30 mL of water twice and then dried over anhydrous Na2SO4 before the solvent was removed. The obtained brown oil was passed through a column of silica gel with hexane/dichloromethane (v/v, 3/2) as the eluent. The solvent was removed to give a yellow oil (2.3 g, 75.7% yield).

Workup

  1. temperaturethe mixture was heated
  2. customwas removed by a rotary evaporator
  3. additionDichloromethane (50 mL) was added
  4. addition100 mL of ice water was added dropwise
  5. washThe organic layer was further washed with 30 mL of water twice
  6. dry with materialdried over anhydrous Na2SO4 before the solvent
  7. customwas removed
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-7f5b05870e744dccb462cdd71e47d5aa
Source dataset
uspto-grants-2013_12
Patent number
US08598450B2

Reaction notes

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