Piperazine → HCID 90456179, compound

HRID 2202101Notes

Reaction equation

HRID 2202101 reaction equation
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)#[C-:2].[O:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].N1CCNCC1>O1CCCC1>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:3]2[N:1]=[CH:2][O:22][C:23]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:11][CH:10]=1)#[N:9]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 70211Ethyl oxoacetateHCID 1317357244-(Isocyano(tosyl)methyl)benzonitrile

Product 1

HCID 90456179HCID 90456179, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(isocyano(tosyl)methyl)benzonitrile (1 g, 3.37 mmol, 1.00 equiv), ethyl 2-oxoacetate (1 g, 4.90 mmol, 1.45 equiv) and piperazine (500 mg, 5.80 mmol, 1.72 equiv) in tetrahydrofuran (20 mL) was stirred at room temperature overnight. The resulting mixture was concentrated under vacuum and the residue was purified on a silica gel column eluted with 0-30% of ethyl acetate in petroleum ether to afford 0.4 g (49%) of ethyl 4-(4-cyanophenyl)oxazole-5-carboxylate as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 8.27-8.24 (m, 2H), 8.07 (s, 1H), 7.76-7.73 (m, 2H), 4.47-4.36 (m, 2H), 1.43-1.33 (m, 3H) ppm.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customthe residue was purified on a silica gel column
  3. washeluted with 0-30% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-79a651b23391422bb0b8b98b04ac0857
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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