Lawesson's reagent → 4-Cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbothioamide

HRID 17489Notes

Reaction equation

COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([C:25]1[C:30]2[N:31]=[C:32]([C:34]([NH2:36])=O)[O:33][C:29]=2[C:28]([F:37])=[C:27]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:26]=1[CH3:44])#[N:24]>C1(C)C=CC=CC=1>[C:23]([C:25]1[C:30]2[N:31]=[C:32]([C:34](=[S:10])[NH2:36])[O:33][C:29]=2[C:28]([F:37])=[C:27]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:26]=1[CH3:44])#[N:24]

Participants

Conditions

Temperature: 125 °C

Procedure

Lawesson's reagent (458 mg, 1.13 mmol) was added to a toluene solution of 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-196) (304 mg, 1.03 mmol), followed by heating under reflux in an oil bath at 125° C. for 10 minutes. After cooling to room temperature, the reaction liquid was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=20:1→10:1) to obtain the entitled compound (134 mg, 41.8%) as a yellow solid.

Workup

temperatureby heating
temperatureAfter cooling to room temperature
customthe reaction liquid
concentrationwas concentrated
customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform:ethyl acetate=20:1→10:1)

Sources & evidence

ORD record: ord-aa48d38c1d0b4f32810ca3ec04e0401a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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