Water → HCID 86584489, compound

HRID 394941Notes

Reaction equation

HRID 394941 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:19][C:20]([CH3:25])=[CH:21][C:22](Cl)=[O:23].O>C(Cl)(Cl)Cl>[CH3:19][C:20]([CH3:25])=[CH:21][C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 1023943-Methyl-2-butenoyl chlorideHCID 86584488(RS)-ethyl 2-(4-aminophenyl)-heptanoate

Product 1

HCID 86584489HCID 86584489, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.4 g of (RS)-ethyl 2-(4-aminophenyl)-heptanoate dissolved in 100 ml of chloroform was treated dropwise with 4.64 ml of 3,3-dimethylacryloyl chloride. The mixture was heated to reflux for 6 hours. After cooling to room temperature, 100 ml of water were added. The phases were separated and the aqueous phase was extracted with two portions of 50 ml of chloroform. The combined organic extracts were washed with two portions of 100 ml of saturated aqueous sodium bicarbonate solution and one portion of 100 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated in vacuo. The product was used without purification. 1H NMR (CDCl3): 7.48 (br. d, J=8.4 Hz, 2H), 7.39 (br. s, 1H), 7.24 (d, J=8.5 Hz, 2H), 5.71 (br. s, 1H), 4.20-4.00 (m, 2H), 3.48 (t, J=7.7 Hz, 1H), 2.21 (br. s, 3H), 2.15-1.95 (m, 1H), 1.87 (s, 3H), 1.80-1.65 (m, 1H), 1.35-1.15 (m, 6H), 1.20 (t, J=7.1 Hz, 3H), 0.85 (t, J=6.7 Hz, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with two portions of 50 ml of chloroform
  5. washThe combined organic extracts were washed with two portions of 100 ml of saturated aqueous sodium bicarbonate solution and one portion of 100 ml of saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe product was used without purification

Sources & evidence

ORD record
ord-d46f49955f834abdb392f90bcef21165
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

Loading…