Triethylamine → HCID 66572312, compound

HRID 75843Notes

Reaction equation

HRID 75843 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12](/[C:13](/Cl)=[N:14]\[OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[C:27]#[CH:28]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]2[CH:28]=[C:27]([C:26]([O:30][CH2:31][CH3:32])=[O:29])[O:15][N:14]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12182Ethyl propiolateHCID 10901405(1E)-N-hydroxy-4-phenylmethoxybenzenecarboximidoyl chloride

Product 1

HCID 66572312HCID 66572312, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To (E)-4-(benzyloxy)-N-hydroxybenzimidoyl chloride (7.8 g) in Toluene (78 ml), Ethyl propiolate (7.25 ml) was added and stirred. To this, Et3N (4.58 ml) was added dropwise since reaction was exothermic and the reaction mixture was then heated to 80° C. for 2 hours. The reaction mixture was cooled, diluted with Ethyl acetate and washed successively with 0.1M Aqueous HCl, water and brine. Organic layer was collected and concentrated to obtain dark brown residue which was purified by column chromatography (silica gel, DCM) to obtain pale brown solid which was crystallized from DCM-Petroleum ether to obtain the title compound as off white solid. Yield: 2.83 g (29%); MS (ES+): m/z 324 (M+1); 1HNMR (CDCl3; 300 MHz): δ 7.8 (d, 2H), 7.36-7.47 (m, 5H), 7.28 (s, 1H), 7.1 (d, 2H), 5.14 (s, 2H), 4.48 (q, 2H), 1.45 (t, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed successively with 0.1M Aqueous HCl, water and brine
  3. customOrganic layer was collected
  4. concentrationconcentrated
  5. customto obtain dark brown residue which
  6. customwas purified by column chromatography (silica gel, DCM)
  7. customto obtain pale brown solid which
  8. customwas crystallized from DCM-Petroleum ether

Sources & evidence

ORD record
ord-5737acb0d24146cf97b0b0a78c91f7c5
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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