Acetone → HCID 178419520, compound

HRID 1979811Notes

Reaction equation

HRID 1979811 reaction equation
Br.[Br:2][C:3]1[N:4]=[C:5]([CH3:11])[NH:6][C:7]=1[C:8](=O)[CH3:9].C(=O)(O)[O-].[Na+].CC(C)=O.[C:21]([NH:24][C:25]([NH2:27])=[S:26])(=[NH:23])[NH2:22]>O>[BrH:2].[NH:24]([C:25]1[S:26][CH:9]=[C:8]([C:7]2[N:6]=[C:5]([CH3:11])[NH:4][CH:3]=2)[N:27]=1)[C:21]([NH2:23])=[NH:22]

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 178419567HCID 178419567, compoundHCID 178513045HCID 178513045, compound

Product 1

HCID 178419520HCID 178419520, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.8 g (9.86 mmol) of 4-bromo-acetyl-2-methylimidazole hydrobromide was dissolved in 10 ml water. Saturated sodium bicarbonate solution was added to pH 10 and the resultant solid was collected by filtration and washed with 15 ml water. The dried free base was heated at reflux in 50 ml acetone. To the refluxing clear acetone solution was added 1.2 g (9.86 mmol) of amidinothiourea. Solution occurred immediately and within a minute a solid began to form. After one hour reflux the slurry was cooled and the solid was collected by filtration and was washed with acetone followed by ether to give 2.37 g (79%) of the title compound, M.P. 158° (dec.); nmr (DMSO-d6) (delta): 7.71 (s shoulder on broad s, 1H); 7.56 (broad s, 4H); 4.32 (s, 1H); 2.51 (s, 3H).

Workup

  1. filtrationthe resultant solid was collected by filtration
  2. washwashed with 15 ml water
  3. temperatureThe dried free base was heated
  4. temperatureat reflux in 50 ml acetone
  5. customto form
  6. temperatureAfter one hour reflux the slurry
  7. temperaturewas cooled
  8. filtrationthe solid was collected by filtration
  9. washwas washed with acetone

Sources & evidence

ORD record
ord-67e3f08b7d52497aa18b5caf78f23f75
Source dataset
uspto-grants-1984_11
Patent number
US04482723

Reaction notes

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