Reaction #2254159

ord-8d6ddd41ccfc452b9896e2f5d98b0224

Reaction equation

O=C(O)c1cc(Cl)cc(Cl)c1NC(=O)c1cc(C(F)(F)F)nn1-c1ncccc1Cl
2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-hydroxycarbonyl-phenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide
CC(=O)OC(C)=O
acetic anhydride
O=c1oc(-c2cc(C(F)(F)F)nn2-c2ncccc2Cl)nc2c(Cl)cc(Cl)cc12
title compound
Yield 57.1%
O=c1oc(-c2cc(C(F)(F)F)nn2-c2ncccc2Cl)nc2c(Cl)cc(Cl)cc12
6,8-dichloro-2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]benzo[d][1,3]oxazin-4-one
Yield 57.1%

Conditions

Temperature
55°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe resulting solid was filtered
  2. 2
    Washwashed with cold methylene chloride

Procedure

To a solution of 2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-hydroxycarbonyl-phenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide (18.4 g, 38.3 mmol) in methylene chloride (130 mL) was added acetic anhydride (39.4 mL, 417 mmol). The reaction was then heated to 55° C. for 2 h and then stirred for a further 16 h at room temperature. The resulting solid was filtered and washed with cold methylene chloride. Trituration with diethyl ether afforded the title compound (10.1 g, 57%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09044016B2uspto-grants-2015_06