Ethanol → HCID 66700089, compound

HRID 1910720Notes

Reaction equation

HRID 1910720 reaction equation
[CH3:1][CH:2]1[NH:7][C:6]2[CH:8]=[CH:9][S:10][C:5]=2[C:4](=[O:11])[CH2:3]1.N1C=CC=CC=1.[C:18](Cl)(=[O:20])[CH3:19].C(O)C>ClCCl>[C:18]([N:7]1[CH:2]([CH3:1])[CH2:3][C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]1=2)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 6367Acetyl chlorideHCID 66700165HCID 66700165, compound

Product 1

HCID 66700089HCID 66700089, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[Step 4] 123 mg (0.74 mmol) of the 5-methyl-5,6-dihydrothieno[3,2-b]pyridin-7(4H)-one were dissolved in 4 mL of anhydrous dichloromethane followed by sequentially adding 0.12 mL (1.5 mmol) of anhydrous pyridine and 0.078 mL (1.1 mmol) of acetyl chloride and stirring for 1 hour at room temperature. Following completion of the reaction, ethanol was added, the solution was concentrated under reduced pressure and then additionally boiled with toluene. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain 111 mg of 4-acetyl-5-methyl-5,6-dihydrothieno[3,2-b]pyridin-7(4H)-one in the form of a pale brown oil (72%).

Workup

  1. additionwas added
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c3e53275424b4f05b77fd477b66020e6
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

Loading…