Ammonia → 3-amino-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

HRID 993152Notes

Reaction equation

[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([NH:8][C:9](=[O:14])[C:10]2([CH3:13])[O:12][CH2:11]2)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-:3])=[O:2].[NH3:21]>CO>[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([NH:8][C:9](=[O:14])[C:10]([OH:12])([CH3:13])[CH2:11][NH2:21])=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-:3])=[O:2]

Participants

Conditions

Temperature: -70 °C

Procedure

A pressure reactor was charged with 4-nitro-3-trifluoromethyl-N-[2,3-epoxy-2-methyl propionyl]aniline, BP-33, (10.0 g, 34.46 mmol) (see FIG. 3) and methanol (100 mL). After cooling to −70° C., ammonia in excess was condensed into the reactor which was sealed and stirred 14 hours. Following evaporation, the crude solid was washed with cold CH2Cl2 (50 mL). Filtration and drying gave 6.1 g BP-34 (58% yield).

Workup

customcondensed into the reactor which
customwas sealed
customevaporation
washthe crude solid was washed with cold CH2Cl2 (50 mL)
filtrationFiltration
customdrying
customgave 6.1 g BP-34 (58% yield)

Sources & evidence

ORD record: ord-4e6e7c77a9ef40098bb2364e07ce4106
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472415B1

Reaction notes

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