Ethyl trifluoroacetate → HCID 885871, compound

HRID 491502Notes

Reaction equation

HRID 491502 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15]>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][C:14](=[O:15])[C:13]([F:20])([F:19])[F:12])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

5

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 663013,5-Dimethoxyaniline

Product 1

HCID 885871HCID 885871, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 3,5-dimethoxyaniline (20 g, 131 mmol) dissolved in anhydrous tetrahydrofuran (90 mL) was added 4-(dimethylamino)pyridine (1.6 g, 13.1 mmol) and ethyl trifluoroacetate (47 mL, 392 mmol). After refluxing 48 hours, the cooled reaction mixture was concentrated and partitioned between ethyl acetate (300 mL) and 2N hydrochloric acid (100 mL). The ethyl acetate layer was washed with water (100 mL), dried using anhydrous sodium sulfate, and concentrated to yield N-(3,5-Dimethoxy-phenyl)-2,2,2-trifluoro-acetamide (31.8 g, 98%) as pale yellow solid.

Workup

  1. temperatureAfter refluxing 48 hours
  2. customthe cooled reaction mixture
  3. concentrationwas concentrated
  4. custompartitioned between ethyl acetate (300 mL) and 2N hydrochloric acid (100 mL)
  5. washThe ethyl acetate layer was washed with water (100 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7ac633bfe87c43b682c9205e6f8b21b5
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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