Methyl trifluoroacetate → 2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide

HRID 728220Notes

Reaction equation

[CH2:1]([NH2:4])[C:2]#[CH:3].[F:5][C:6]([F:12])([F:11])[C:7](OC)=[O:8]>>[CH2:1]([NH:4][C:7](=[O:8])[C:6]([F:12])([F:11])[F:5])[C:2]#[CH:3]

Participants

Reactant 2

HCID 9893Methyl trifluoroacetate

HCID 239041Propargylamine

Product 1

HCID 110948052,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamideYield 91.4%

Procedure

Propargylamine (24.79 g, 0.450 mole; Aldrich, 99%) was added dropwise over 1 h to methyl trifluoroacetate (69.19 g, 0.540 mole, 1.2 eq, Aldrich) at 0°. After stirring an additional hour at 0°, distillation though a 15 cm Vigreux column afforded 62.12 g (91%) of trifluoroacetamide 43 as a colorless liquid (bp 68.5°-69.5° at 11 torr). This material was homogeneous by NMR and GC and was used interchangeably with spectroscopically-identical material prepared by acylating propargylamine with trifluoroacetic acid anhydride.

Workup

distillationdistillation though a 15 cm Vigreux column

Sources & evidence

ORD record: ord-a582dd79fa2a451eb4bffe65d42f4332
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047519

Reaction notes

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