Oxalyl chloride → 3-[5-(2-Fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoyl isocyanate

HRID 920885Notes

Reaction equation

C(Cl)(=O)[C:2](Cl)=[O:3].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([NH2:24])=[O:23])[N:15]=1>ClCCl>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([N:24]=[C:2]=[O:3])=[O:23])[N:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Oxalyl chloride (2.5 ml, 28.2 mmol, 2.0 eq.) is then added dropwise under N2 to a suspension of 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzamide (Compound A3, 4.0 g, 14.1 mmol) in anhydrous dichloromethane (20 mL) cooled to 0° C. The mixture is slowly heated to reflux and stirred for an additional 6 h. The solvent is removed on a rotary evaporator. The residue is azeotroped with anhydrous dichloromethane (20 mL) and dried under high vacuum for two hours to give 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoyl isocyanate (Compound A4) as a tan solid 4.12 g (95%) which may be used immediately without further purification.

Workup

temperatureThe mixture is slowly heated
temperatureto reflux
customThe solvent is removed on a rotary evaporator
customThe residue is azeotroped with anhydrous dichloromethane (20 mL)
customdried under high vacuum for two hours

Sources & evidence

ORD record: ord-23ae54c8ddce408c81d91bad5b52d52b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273076B2

Reaction notes

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