Benzoyl isothiocyanate → HCID 18693723, compound

HRID 1870831Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:13]2[CH:17]=[C:16]([NH2:18])[O:15][N:14]=2)[CH3:12])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)CCl>[C:19]([NH:27][C:28]([NH:18][C:16]1[O:15][N:14]=[C:13]([CH:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=2)[CH3:12])[CH:17]=1)=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

This isoxazol (11.35 g) was dissolved in ethylene dichloride (200 ml) and then benzoyl isothiocyanate (11.9 ml) was added, after which the resulting mixture was stirred at 60° C. for 5 hours. The reaction mixture was concentrated under reduced pressure and a small amount of water was added, after which the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was isolated by a silica gel column chromatography (hexane/ethyl acetate=2/1) and then purified by a recrystallization method from toluene, to obtain 1-benzoyl-3-{3-[1-(4-isobutyl-phenyl)-ethyl]-isoxazol-5-yl}-thiourea (4.65 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additiona small amount of water was added
extractionafter which the resulting mixture was subjected to extraction with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was isolated by a silica gel column chromatography (hexane/ethyl acetate=2/1)
custompurified by a recrystallization method from toluene

Sources & evidence

ORD record: ord-c7daf83de96441adbd2065fc2342f54c
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06100260

Reaction notes

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