Acetic Acid → HCID 85765793, compound

HRID 325044Notes

Reaction equation

HRID 325044 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[CH:3]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].C(O)(=O)C>>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][O:9][C:4]2[CH:3]=[C:2]([NH:1][CH:21]([CH3:22])[C:20]([O:24][CH2:25][CH3:26])=[O:23])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[CH:17][CH:16]=1)#[N:19]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 22033482HCID 22033482, compound

Product 1

HCID 85765793HCID 85765793, compoundYield 29%

Procedure

Amino-3-[2-(4-cyanophenyl)ethoxy]-5-methylbenzene (0.252 g; 1.00 mmol; from Example 17(iii) above), ethyl acrylate (130 μL; 1.2 mmol) and acetic acid (9 μL; 0.15 mmol) were refluxed together for 8 hours. After evaporation in vacuo, the resultant black oil was purified by flash chromatography (SiO2; EtOAc:heptane (3:7)) to give 0.102 g (29%) of the sub-title compound.

Workup

  1. customAfter evaporation in vacuo
  2. customthe resultant black oil was purified by flash chromatography (SiO2; EtOAc:heptane (3:7))

Sources & evidence

ORD record
ord-7a56cfcbbe524a63a8f6c6a9217297cf
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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