Acetone → HCID 68323863, compound

HRID 573538Notes

Reaction equation

HRID 573538 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:6]=1[C:7]#[N:8].[CH3:18][C:19]([CH3:21])=O.Cl[Sn](Cl)(Cl)Cl>C1(C)C=CC=CC=1.[OH-].[Na+]>[CH3:17][C:4]1[S:3][C:2]2[N:1]=[C:19]([CH3:21])[CH:18]=[C:7]([NH2:8])[C:6]=2[C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 24287Tin tetrachlorideHCID 672368862-Amino-5-methyl-4-[3-(methyloxy)phenyl]-3-thiophenecarbonitrile

Product 1

HCID 68323863HCID 68323863, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-amino-5-methyl-4-[3-(methyloxy)phenyl]-3-thiophenecarbonitrile (Description 3) (260 mg, 1.064 mmol) in toluene (2.5 mL), were added at RT, acetone (0.094 mL, 1.277 mmol) and SnCl4 (0.150 mL, 1.277 mmol), the reaction mixture was stirred for 5 min at RT then for 15 min at 150° C. in a microwave. The reaction mixture was cooled to RT then diluted with aqueous NaOH (1M) until the solution turned basic. The aqueous layer was then extracted with DCM (3×30 mL), the combined organic extracts were dried over a phase separating column and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, afforded the title compound (167 mg). LCMS (A) m/z: 285 [M+1]+, Rt 1.20 min (basic).

Workup

  1. extractionThe aqueous layer was then extracted with DCM (3×30 mL)
  2. customthe combined organic extracts were dried over a phase
  3. customseparating column
  4. concentrationconcentrated
  5. customPurification by chromatography on silica gel
  6. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-132fc27a69234ff98a594ff5968218af
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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