Trifluoroacetic anhydride → Acetic acid, trifluoro-, (methylnitroamino)methyl ester

HRID 2081920Notes

Reaction equation

HRID 2081920 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([O:5][C:6](=O)C(F)(F)F)=[O:4].O[CH2:15][N:16]([N+:18]([O-:20])=[O:19])C>ClCCl>[F:1][C:2]([F:13])([F:12])[C:3]([O:5][CH2:6][N:16]([N+:18]([O-:20])=[O:19])[CH3:15])=[O:4]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 119262Methanol, (methylnitramino)-

Product 1

HCID 13352131Acetic acid, trifluoro-, (methylnitroamino)methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (80 ml, 118.4 g, 0.56 moles) was added to a stirred solution of 1-hydroxy-2-nitro-2-azapropane (40.0 g, 0.38 moles) in dichloromethane (60 ml) at -5° to 0° C. during 11/2 hours. The resulting solution was then distilled without warming at 20 mm, then to 3 mm. The product was distilled at 1.5 mm, 65° C., to give 2-nitro-2-azapropyl trifluoroacetate; yield: 48 g (63%).

Workup

  1. distillationThe resulting solution was then distilled
  2. temperaturewithout warming at 20 mm
  3. distillationThe product was distilled at 1.5 mm, 65° C.

Sources & evidence

ORD record
ord-7d85e6541fa64edb93056774a4eb11f3
Source dataset
uspto-grants-1993_02
Patent number
US05186770

Reaction notes

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