Lawesson's reagent → 2-(4-Cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylethanethioamide

HRID 17606Notes

Reaction equation

COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:10]2)=CC=1.[C:23]([C:25]1[C:30]2[N:31]=[C:32]([CH:34]3[CH2:36][CH2:35]3)[O:33][C:29]=2[C:28]([CH2:37][C:38]([N:40]([CH3:42])[CH3:41])=O)=[C:27]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:26]=1[CH3:49])#[N:24]>C1(C)C=CC=CC=1>[C:23]([C:25]1[C:30]2[N:31]=[C:32]([CH:34]3[CH2:36][CH2:35]3)[O:33][C:29]=2[C:28]([CH2:37][C:38](=[S:10])[N:40]([CH3:42])[CH3:41])=[C:27]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:26]=1[CH3:49])#[N:24]

Participants

Conditions

Temperature: 125 °C

Procedure

2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide (24.8 mg, 0.061 mmol) was added to a toluene (1 ml) solution of 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamide (I-313) (20.0 mg, 0.056 mmol), followed by stirring in ah oil bath at 125° C. for 5 hours. The reaction liquid was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1, v/v) to obtain the entitled compound (14.0 mg, 67%) as a yellow solid.

Workup

customThe reaction liquid
concentrationwas concentrated
customthe resulting residue was purified by silica gel column chromatography (eluent, n-hexane

Sources & evidence

ORD record: ord-18607ce00ccb4bd782da06663c299825
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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