Ethyl propiolate → HCID 68515710, compound

HRID 1717386Notes

Reaction equation

HRID 1717386 reaction equation
[N:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([NH:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[O:9])=[CH:6][C:5]=1[I:18])=[N+:2]=[N-:3].[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[C:20]#[CH:21]>C1(C)C=CC=CC=1>[I:18][C:5]1[CH:6]=[C:7]([C:8]([NH:10][CH2:11][C:12]([F:14])([F:15])[F:13])=[O:9])[CH:16]=[CH:17][C:4]=1[N:1]1[CH:21]=[C:20]([C:19]([O:23][CH2:24][CH3:25])=[O:22])[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 86629813HCID 86629813, compound

Product 1

HCID 68515710HCID 68515710, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-azido-3-iodo-N-(2,2,2-trifluoroethyl)benzamide (2.93 g, 7.92 mmol) obtained in Example 379b) in toluene (80 ml) was added ethyl propiolate (2.33 g, 23.7 mmol), the reaction mixture was stirred with heating under reflux for 18 hr. After cooling to room temperature, the precipitate was collected by filtration, washed with hexane and dried to give the title compound as a pale-yellow powder (2.80 g, 76%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 18 hr
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-e3503b9d0bc14254a6ac5f761ad2d241
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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