Ethyl propiolate → HCID 178472243, compound

HRID 624649Notes

Reaction equation

HRID 624649 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[NH:9])[NH:7][OH:8])=[C:4]([F:12])[CH:3]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15]>>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[NH:9])[NH:7][O:8][CH:15]=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([F:12])[CH:3]=1

Participants

3

Reactant 2

HCID 12182Ethyl propiolateHCID 178513303HCID 178513303, compound

Product 1

HCID 178472243HCID 178472243, compoundYield 95.9%

Conditions

Temperature
30 °C

Procedure

To a solution of 4-chloro-2-fluoro-N-hydroxybenzimidamide 39 (378 g, 2 mol, 1.0 eq) and Amberlyst® A21 (20 wt %, 75.6 g) in toluene PhMe (5.6 L, 15 vol) was added ethyl propiolate (275 g, 2.8 mol, 1.4 eq) at 30° C. The reaction was stirred at 30° C. overnight and checked by LC-MS. Reaction was then filtered and the filtrate was concentrated under vacuum, and 550 g ethyl 3-(4-chloro-2-fluorobenzimidamidooxy)acrylate 40 was obtained as a yellow oil with 83% LC purity (Scheme 15).

Workup

  1. customReaction
  2. filtrationwas then filtered
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-576533765ef54420b6297e4922f1d8a0
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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