Thiobenzamide → HCID 70818685, compound

HRID 590982Notes

Reaction equation

HRID 590982 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]([NH2:23])(=[S:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1>[O:13]1[C:8]2[CH:7]=[CH:6][C:5]([C:3]3[N:23]=[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[S:22][CH:2]=3)=[CH:14][C:9]=2[CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 6504217HCID 6504217, compound

Product 1

HCID 70818685HCID 70818685, compoundYield 94.1%

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) (250 mg, 1.19 mmol) and thiobenzamide (180 mg, 1.3 mmol) in dioxane (10 mL) was refluxed for 15 hours, then the reaction mixture was concentrated. 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 (dichloromethane/cyclohexane 60/40) to afford the desired thiazole (9c) as a white solid (330 mg, 1.12 mmol, 94%).

Workup

  1. concentrationthe reaction mixture was concentrated
  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 (dichloromethane/cyclohexane 60/40)

Sources & evidence

ORD record
ord-acad0a51e02441a9a5cd8cb33fa0541a
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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