Thioacetamide → HCID 70818377, compound

HRID 591001Notes

Reaction equation

HRID 591001 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:14]=1)=O.[C:15]([NH2:18])(=[S:17])[CH3:16]>O1CCOCC1>[O:13]1[C:8]2[CH:7]=[CH:6][C:5]([C:3]3[N:18]=[C:15]([CH3:16])[S:17][CH:2]=3)=[CH:14][C:9]=2[CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 6504217HCID 6504217, compound

Product 1

HCID 70818377HCID 70818377, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloro-1-(3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one (9b) (270 mg, 1.28 mmol) and thioacetamide (106 mg, 1.41 mmol) in dioxane (10 mL) was refluxed for 20 hours, then the reaction mixture was concentrated in vacuo. The residue was diluted with dichloromethane (20 mL), washed with water (10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired thiazole (13a) as a yellow oil (260 mg, 1.12 mmol, 88%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with dichloromethane (20 mL)
  3. washwashed with water (10 mL), brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-d061f8e9e39c409d82fd3e5739c2f39e
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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