Water → HCID 68157460, compound

HRID 1473802Notes

Reaction equation

[C:1]1([CH3:35])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([NH:10]/[N:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]=[CH:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1)=[S:9].[CH2:36](N(CC)CC)C.Cl[CH2:44][C:45](=O)[CH3:46].O>CC(=O)CC>[CH3:35][C:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:36])[C:2]=1[N:7]1[C:45]([CH3:46])=[CH:44][S:9]/[C:8]/1=[N:10]/[N:11]=[CH:12]\[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]=[CH:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=3)[N:20]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of (E)-N-(o-tolyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide (257 mg, 0.520 mmol) in butanone (5 mL) was added triethylamine (0.14 mL, 1.0 mmol) and chloroacetone (0.06 mL, 0.73 mmol) and refluxed at 75° C. for 15 h. The mixture was allowed to cool to room temperature and then transferred to a separatory funnel containing water (5 mL) and extracted twice with dichloromethane. The organic layers were filtered through a phase separator, adsorbed onto silica gel, and purified by flash column chromatography to afford the title compound as a yellow solid (229 mg, 83%): mp 87° C. (dec); 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.19-8.15 (m, 3H), 7.82-7.75 (m, 4H), 7.43-7.30 (m, 5H), 7.24 (d, J=7.3 Hz, 1H), 5.88 (d, J=1.3 Hz, 1H), 2.21 (s, 3H), 1.80 (d, J=1.2 Hz, 3H); ESIMS m/z 536 (M+H).

Workup

temperatureto cool to room temperature
customtransferred to a separatory funnel
extractionextracted twice with dichloromethane
filtrationThe organic layers were filtered through a phase separator
custompurified by flash column chromatography

Sources & evidence

ORD record: ord-9473123484f844a7ba5883933a82f09d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018136B2

Reaction notes

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