1,1'-Thiocarbonyldiimidazole → N-(4-Fluoro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

HRID 1410225Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][NH:6][C:7]([C:9]1([C:12]([F:15])([F:14])[F:13])[CH2:11][CH2:10]1)=[O:8].C1N=CN([C:25](N2C=NC=C2)=[S:26])C=1>C(Cl)Cl>[F:19][C:18]1[CH:17]=[CH:16][C:4]([CH2:5][NH:6][C:7]([C:9]2([C:12]([F:13])([F:14])[F:15])[CH2:10][CH2:11]2)=[O:8])=[CH:3][C:2]=1[N:1]=[C:25]=[S:26]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(3-amino-4-fluorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide (3.17 g; 11.5 mmol) and TCDI (3.07 g; 17.2 mmol) in DCM (50 mL) was heated over night at 50° C. The mixture was concentrated and the residue purified by column chromatography to give the sub-title compound. Yield: 3 g (82%).

Workup

concentrationThe mixture was concentrated
customthe residue purified by column chromatography

Sources & evidence

ORD record: ord-d248b5c7236d44b5ae486fbdf48271cd
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921405B2

Reaction notes

Loading…