p-(Trifluoromethoxy)phenyl isocyanate → HCID 59363501, compound

HRID 1957928Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-])=O)[CH:4]=[C:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].C([O-])=O.[NH4+].[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(OCC)(=O)C.C(O)C.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:23][CH:24]=2)=[O:30])[CH:4]=[C:3]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

304 mg (1.53 mmol) of ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate are initially charged in 6 ml of ethyl acetate/ethanol (1:1), 163 mg (0.15 mmol) of palladium (10% on activated carbon) and 580 mg (9.20 mmol) of ammonium formate are added, and the mixture is stirred at 80° C. for 1 h. After cooling, the mixture is filtered through kieselguhr, the filtercake is rinsed with ethanol and the filtrate is freed from the solvent under reduced pressure. The residue is dissolved in 6 ml of THF, 374 mg (1.84 mmol) of 4-trifluoromethoxyphenyl isocyanate are added and the mixture is stirred at RT for 1 h. The reaction solution is concentrated and the residue is purified by RP-HPLC (acetonitrile/water). This gives a solid.

Workup

temperatureAfter cooling
filtrationthe mixture is filtered through kieselguhr
washthe filtercake is rinsed with ethanol
dissolutionThe residue is dissolved in 6 ml of THF
stirringthe mixture is stirred at RT for 1 h
concentrationThe reaction solution is concentrated
customthe residue is purified by RP-HPLC (acetonitrile/water)
customThis gives a solid

Sources & evidence

ORD record: ord-e5518b05fa734e4398a821c115047757
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410090B2

Reaction notes

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