Acetamide → HCID 77230839, compound

HRID 2203318Notes

Reaction equation

HRID 2203318 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].Cl[CH2:6][C:7](=O)[CH2:8][C:9]([O:11][CH3:12])=[O:10]>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:2][C:1]1[O:3][CH:6]=[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[N:4]=1

Participants

5

Reactant 2

HCID 178AcetamideHCID 36240Methyl 4-chloroacetoacetate

Product 1

HCID 77230839HCID 77230839, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of acetamide (1.312 g, 22.21 mmol) and methyl chloroacetoacetate in 20 mL of 1,4-dioxane and 20 mL of toluene was heated at 120° C. for 4 hours. The solution was concentrated and the residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated compound (a pale yellow oil). 1H NMR (CDCl3, 500 MHz) δ 7.58 (1H, s), 3.78 (3H, s), 3.64 (2H, s), 2.51 (3H, s).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by silica gel chromatography
  3. customto give the indicated compound (a pale yellow oil)

Sources & evidence

ORD record
ord-70670c7a7bf942bc935109a998638ee5
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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