1,1,3,3-Tetramethylguanidine → HCID 178467224, compound

HRID 1262675Notes

Reaction equation

HRID 1262675 reaction equation
Br[C:2](=[CH:6]OCC)[C:3](=[O:5])[CH3:4].Cl.[OH:11][CH2:12][C:13]([NH2:15])=[NH:14].CN(C)C(N(C)C)=N>CC(C)=O>[OH:11][CH2:12][C:13]1[NH:14][CH:6]=[C:2]([C:3](=[O:5])[CH3:4])[N:15]=1

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 122173662-Hydroxy-acetamidine hydrochlorideHCID 534237433-Bromo-4-ethoxybut-3-EN-2-one

Product 1

HCID 178467224HCID 178467224, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9.7 g (0.05 mol) of 3-bromo-4-ethoxy-3-buten-2-one was combined with 5.53 (0.05 mol) of hydroxyacetamidine hydrochloride in 100 ml acetone to form a slurry. To the slurry at 25° was added 11.5 g (0.1 mol) of 1,1,3,3-tetramethylguanidine over a period of 5 minutes. After stirring for 48 hours the slurry was filtered and the mother liquors were concentrated in vacuo to an oil which was chromatographed on silica gel 60 (E. Merck) using chloroform as eluent to give 1.48 g (21%) of 2-hydroxymethyl-4-acetylimidazole, mp 147°-148°. nmr (DMSO-d6) (δ): 7.73 (s, 1H); 5.46 (very broad s, 1H); 4.5 (broad s, 2H); 2.4 (s, 3H).

Workup

  1. customto form a slurry
  2. filtrationwas filtered
  3. concentrationthe mother liquors were concentrated in vacuo to an oil which
  4. customwas chromatographed on silica gel 60 (E. Merck)

Sources & evidence

ORD record
ord-5927808fd2dd4a99a26aed0dc5534959
Source dataset
uspto-grants-1984_06
Patent number
US04452987

Reaction notes

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