3-(Dimethylamino)-2-methyl-2-propenal → HCID 68751373, compound

HRID 1912973Notes

Reaction equation

HRID 1912973 reaction equation
[C:1]([C:5]1[C:6]([NH2:11])=[N:7][NH:8][C:9]=1[NH2:10])([CH3:4])([CH3:3])[CH3:2].CN(C)[CH:14]=[C:15]([CH3:18])[CH:16]=O>C(O)C.C(O)(=O)C>[C:1]([C:5]1[C:6]([NH2:11])=[N:7][N:8]2[CH:16]=[C:15]([CH3:18])[CH:14]=[N:10][C:9]=12)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 5658623-(Dimethylamino)-2-methyl-2-propenalHCID 68753336HCID 68753336, compound

Product 1

HCID 68751373HCID 68751373, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture from Example 105A (1.56 g, 10.1 mmol), 3-dimethylamino-2-methyl-2-propenal (1.63 g, 14.4 mmol) and acetic acid (25 μL, 0.44 mmol) in ethanol (10 mL) was heated by microwave to 150° C. for 30 minutes. The mixture was cooled to ambient temperature and concentrated. Purification by silica gel chromatography (EtOAc, Rf=0.53) afforded 1.66 g (80%) of the title compound. MS (DCI) m/z 205 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customPurification by silica gel chromatography (EtOAc, Rf=0.53)

Sources & evidence

ORD record
ord-9c123abddf514d7fbde98d57eafe44fd
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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