Acetyl chloride → HCID 118023539, compound

HRID 2171785Notes

Reaction equation

HRID 2171785 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:16](Cl)(=O)[CH3:17]>C1COCC1>[CH:10]1([C:4]2[S:3][C:2]3[N:1]=[C:16]([CH3:17])[NH:9][C:7](=[O:8])[C:6]=3[CH:5]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 80400357HCID 80400357, compound

Product 1

HCID 118023539HCID 118023539, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-amino-5-cyclohexylthiophene-3-carboxamide (53.5 g) and THF (500 mL) were added dropwise acetyl chloride (18 mL) and TEA (36 mL) under ice-cooling, followed by stirring at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added EtOH (500 mL) and a 1 M aqueous NaOH solution (500 mL), followed by stirring at 80° C. for 24 hours. The reaction mixture was left to be cooled to room temperature, and 1 M hydrochloric acid (500 mL) was added thereto, followed by stirring. The precipitate was collected by filtration, washed with water, and dried by blowing air to obtain 6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4(3H)-one (57.0 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue were added EtOH (500 mL)
  4. stirringby stirring at 80° C. for 24 hours
  5. waitThe reaction mixture was left
  6. temperatureto be cooled to room temperature
  7. addition1 M hydrochloric acid (500 mL) was added
  8. stirringby stirring
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-decf9bc76a2c4e28b7d05e2508efac06
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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