Dimethylformamide dimethyl acetal → HCID 67435184, compound

HRID 1663413Notes

Reaction equation

HRID 1663413 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[C:9](=[CH:16][N:17]([CH3:19])[CH3:18])[C:10](=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 149879931-(2-Chlorophenyl)butane-1,3-dione

Product 1

HCID 67435184HCID 67435184, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of crude 1-(2-chlorophenyl)butane-1,3-dione from the previous step and 1,1-dimethoxy-N,N-dimethylmethanamine (2.042 g, 17.14 mmol) in toluene (20 mL) was heated to reflux for 2 h and concentrated. Silica gel chromatography, using 70 to 100% ethyl acetate in hexanes gradient, gave 1-(2-chlorophenyl)-2-((dimethylamino)methylene)butane-1,3-dione as a red, viscous oil (2.20 g, 51% yield for 2 steps). MS (ES+) m/z: 252 (M+H); HPLC retention time: 2.51 min (Analytical HPLC Method D).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c1a3458a245b47feb21a7ba557415bb9
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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