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

HRID 634850Notes

Reaction equation

HRID 634850 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

4

Reactant 2

HCID 222AmmoniaHCID 140648402-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]oxirane-2-carboxamide

Product 1

HCID 100180753-amino-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamideYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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) 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 (5 mL). Filtration and drying gave 6.1 g BP-34 (58% yield).

Workup

  1. customcondensed into the reactor which
  2. customwas sealed
  3. customevaporation
  4. washthe crude solid was washed with cold CH2Cl2 (5 mL)
  5. filtrationFiltration
  6. customdrying
  7. customgave 6.1 g BP-34 (58% yield)

Sources & evidence

ORD record
ord-5d8578b7dde149db8ef2d8311db65221
Source dataset
uspto-grants-2001_02
Patent number
US06184249B2

Reaction notes

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