4-Methoxy-2-methylphenyl isothiocyanate → 1-(4-methoxy-2-methylphenyl)-3-(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)thiourea

HRID 62067Notes

Reaction equation

[F:1][C:2]([F:27])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][NH2:26])=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].[N:28]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=1[CH3:39])=[C:29]=[S:30]>O1CCCC1>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([NH:28][C:29]([NH:26][CH2:25][C:22]2[CH:23]=[CH:24][C:19]([C:16]3[N:17]=[CH:18][N:14]([C:11]4[CH:12]=[CH:13][C:8]([O:7][C:2]([F:1])([F:27])[C:3]([F:6])([F:5])[F:4])=[CH:9][CH:10]=4)[N:15]=3)=[CH:20][CH:21]=2)=[S:30])=[C:32]([CH3:39])[CH:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanamine (0.075 mg, 0.20 mmol) in dry tetrahydrofuran (1 mL) was added 1-isothiocyanato-4-methoxy-2-methylbenzene (0.052 mg, 0.29 mmol) and the resulting mixture was stirred at 50° C. for 24 hours. The mixture was concentrated under reduced pressure to give a brown residue, which was purified by flash column chromatography eluting with mixtures of hexanes and ethyl acetate to afford the title compound as a white solid (0.050 g, 46%).

Workup

concentrationThe mixture was concentrated under reduced pressure
customto give a brown residue, which
customwas purified by flash column chromatography
washeluting with mixtures of hexanes and ethyl acetate

Sources & evidence

ORD record: ord-a8d37bf5a099445397831a029d91adea
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09445594B2

Reaction notes

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