Triethylamine → HCID 86711952, compound

HRID 1475261Notes

Reaction equation

HRID 1475261 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.[C:16]([O:20][CH3:21])(=[O:19])[C:17]#[CH:18].CCN(CC)CC>C1(C)C=CC=CC=1.CCOC(C)=O>[F:12][C:11]([F:14])([F:13])[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]2[CH:18]=[C:17]([C:16]([O:20][CH3:21])=[O:19])[O:1][N:2]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13536Methyl propiolateHCID 86210273HCID 86210273, compound

Product 1

HCID 86711952HCID 86711952, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of N-hydroxy-4-(trifluoromethoxy)benzimidoyl chloride (1.2 g, 5 mmol) and methyl propiolate (0.9 mL, 10 mmol) in toluene (12 mL) was added Et3N (0.73 mL, 5.3 mmol) dropwise over 10 minutes. The resulting reaction mixture was heated at 80° C. for 2.5 h and then diluted with EtOAc (20 mL). The organic layer was washed with 0.1 M aq. HCl, H2O, and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was crystallized from CHCl3 and petroleum ether to afford the title compound (1.1 g, 77%). MS (ES+) C12H8F3NO4 requires: 287. found: 288 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 7.88 (d, J=6.8 Hz, 2H), 7.33 (d, J=6.8 Hz, 2H), 7.25 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with 0.1 M aq. HCl, H2O, and brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from CHCl3 and petroleum ether

Sources & evidence

ORD record
ord-1207ec5e7fdf48488999a77f5d7cb20c
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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