Ethyl propiolate → HCID 59252478, compound

HRID 237886Notes

Reaction equation

HRID 237886 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH:15]3[O:19][C:18]([NH2:20])=[N:17][CH2:16]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21](OCC)(=[O:24])[C:22]#[CH:23]>C(O)C>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH:15]3[O:19][C:18]4=[N:20][C:21](=[O:24])[CH:22]=[CH:23][N:17]4[CH2:16]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 68529232HCID 68529232, compound

Product 1

HCID 59252478HCID 59252478, compoundYield 217.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[(4-cyclohexyl-phenylamino)-methyl]-4,5-dihydro-oxazol-2-ylamine (1.13 g, 4.14 mmol) in 50 ml of ethanol was added 0.42 ml (0.415 mmol) of ethyl propiolate. The mixture was stirred at reflux for 6 h under nitrogen after which it was allowed to cool to room temperature. The resulting white crystals were isolated by filtration, washed with ethanol, and dried at room temperature under high vacuum to provide 0.294 g of the title compound. The filtrate from the filtration was concentrated to 10 ml and allowed to stand for 6 h. The resulting white crystals were isolated by filtration and dried under high vacuum to provide an additional 0.059 g of the title compound.

Workup

  1. temperatureat reflux for 6 h under nitrogen after which it
  2. customThe resulting white crystals were isolated by filtration
  3. washwashed with ethanol
  4. customdried at room temperature under high vacuum

Sources & evidence

ORD record
ord-4b4a5d165c764e05a5fcb78aa7c54a33
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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