Acetonitrile → 143681-37-2

HRID 1180716Notes

Reaction equation

HRID 1180716 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)=O.P([Cl:34])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.C(N(CC)CC)C.C(#N)C>C(OCC)(=O)C>[C:6]1([N:5]=[C:3]([Cl:34])[C:2]([F:17])([F:16])[F:1])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 2676572,2,2-Trifluoro-N-(naphthalen-1-yl)ethanimidic acid

Product 1

HCID 10332712143681-37-2Yield 86.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
82 °C

Procedure

Five grams (20.9 mmol) of 2,2,2-trifluoro-N-(naphthalen-1-yl)acetamide, 11.23 g (41.8 mmol) of diphenyl chlorophosphate, 4.22 g (41.8 mmol) of triethylamine, and 20 ml of acetonitrile were introduced into a 50 ml flask and reacted for 15 hours while being refluxed (82° C.). After the reaction, the reaction solution was cooled to room temperature, 15 ml of ethyl acetate was added thereto, and the precipitate was then filtered off. The filtrate was subjected to solvent removal by evaporation, and the crude product thus obtained was purified by column chromatography (silica gel, ethyl acetate:hexane=3:7), resulting in 4.65 g of N-(naphthalen-1-yl)-2,2,2-trifluoroacetimidoyl chloride as a yellow oil (yield: 86.2%).

Workup

  1. customreacted for 15 hours
  2. customAfter the reaction
  3. temperaturethe reaction solution was cooled to room temperature
  4. filtrationthe precipitate was then filtered off
  5. customThe filtrate was subjected to solvent removal by evaporation
  6. customthe crude product thus obtained
  7. customwas purified by column chromatography (silica gel, ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-39ea0d3e3c554341a22a2ff4df800487
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

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