1,1,3,3-Tetramethylguanidine → HCID 178440051, compound

HRID 1910800Notes

Reaction equation

HRID 1910800 reaction equation
Br[CH2:2][C:3](=O)[C:4]([CH3:15])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)[CH3:5].Cl.[C:18]([NH2:23])(=[NH:22])[CH:19]([CH3:21])[CH3:20].CN(C)C(N(C)C)=N>CN(C=O)C.O>[CH:19]([C:18]1[NH:22][CH:2]=[C:3]([C:4]([CH3:15])([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=2)[CH3:5])[N:23]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 27820532-Methylpropanimidamide hydrochlorideHCID 86639588HCID 86639588, compound

Product 1

HCID 178440051HCID 178440051, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-bromo-3-methyl-3-(3-nitro-phenyl)-butan-2-one (2.28 g, 8.0 mmol), isobutyramidine hydrochloride (3.58 g, 23.7 mmol) and 1,1,3,3-tetramethylguanidine (2.4 mL, 19.1 mmol) in DMF (10 mL) was heated at reflux for 24 h. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated to afford 2-isopropyl-4-[1-methyl-1-(3-nitro-phenyl)-ethyl]-1H-imidazole (0.65 g, 30%) as a cream-coloured solid.

Workup

  1. temperatureat reflux for 24 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-33fe7a16bc884bdbbed40c61202bf198
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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