Lawesson's reagent → HCID 53237678, compound

HRID 1896753Notes

Reaction equation

HRID 1896753 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=O)[CH:19]([CH3:21])[CH3:20])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[S:32])[CH:19]([CH3:21])[CH3:20])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 878297HCID 878297, compound

Product 1

HCID 53237678HCID 53237678, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To N-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)isobutyramide (50 mg, 0.16 mmol) in toluene (2 mL) at 110° C. was added Lawesson's reagent (35 mg, 0.09 mmol). The resulting solution was heated at 110° C. for 7 h. After cooling, the solution was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, then dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 20:80 v/v to afford 13.8 mg (26%) of the title compound (LCMS RT=7.36 min, MH+ 331.2)

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated
  6. customThe resulting solid was purified by column chromatography
  7. washeluting with ethyl acetate/hexanes 20:80 v/v

Sources & evidence

ORD record
ord-8654a44c1ed74717b7cd5a09bbb39edf
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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