Sodium Methoxide → HCID 86668349, compound

HRID 1424741Notes

Reaction equation

[F:1][C:2]([F:38])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:37])[O:27][C:28]4C=CC([N+]([O-])=O)=CC=4)=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].C[O-].[Na+]>CO>[F:38][C:2]([F:1])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:37])[O:27][CH3:28])=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4]

Participants

Conditions

Temperature: -10 °C

Procedure

4-Nitrophenyl 4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenylcarbamate (1.90 g, 3.55 mmol) was slurried in MeOH (15 mL) and cooled in a −10° C. dry ice/acetone bath. Sodium methoxide (1.33 mL of a 30 wt % solution in MeOH, 7.10 mmol) was added dropwise over 10 min. The resulting bright yellow slurry was warmed to ambient temperature and poured into ice water (150 mL). After stirring vigorously for 10 min, the mixture was filtered on a Büchner funnel. The tan solid was rinsed with water and dried in air. Recrystallization from MeOH/water provided the title compound (0.989 g, 65%) as a tan solid: mp 183-184.5° C.; 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H), 8.14 (d, J=8.7 Hz, 2H), 7.79 (d, J=9.0 Hz, 2H), 7.50 (d, J=8.6 Hz, 2H), 7.38 (d, J=8.9 Hz, 2H), 6.79 (s, 1H), 3.80 (s, 3H); HRMS-FAB (m/z) [M+H]+ calcd for C18H13F5N4O3, 428.0908. found, 428.0903.

Workup

temperatureThe resulting bright yellow slurry was warmed to ambient temperature
filtrationthe mixture was filtered on a Büchner funnel
washThe tan solid was rinsed with water
customdried in air
customRecrystallization from MeOH/water

Sources & evidence

ORD record: ord-c7a549f25eaa4eccb0242ffef9e487dc
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927729B2

Reaction notes

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