Acetone → HCID 178419520, compound

HRID 1758749Notes

Reaction equation

HRID 1758749 reaction equation
Br.[CH3:2][C:3]1[NH:4][CH:5]=[C:6]([C:8](=O)[CH2:9][Br:10])[N:7]=1.C(=O)(O)[O-].[Na+].CC(C)=O.[C:21]([NH:24][C:25]([NH2:27])=[S:26])(=[NH:23])[NH2:22]>O>[BrH:10].[NH:24]([C:25]1[S:26][CH:9]=[C:8]([C:6]2[N:7]=[C:3]([CH3:2])[NH:4][CH:5]=2)[N:27]=1)[C:21]([NH2:23])=[NH:22]

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 178419523HCID 178419523, 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 1-(2 -methyl-4-imidazolyl)-2-bromo ethanone 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 1 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 2-guanidino-4-(2-methyl-4-imidazolyl)thiazole hydrobromide, mp 158° (dec.); nmr (DMSO-d6) (δ): 7.71 (s shoulder on broad s, 1H); 7.56 (broad s, 4H); 4.32 (s, 1H); 2.51 (s, 3H); calcd. for C8H10N6S.HBr: C, 31.69; H, 3.66; N, 27.72; found: C, 31.46; H, 4.30; N, 27.28.

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 1 hour reflux the slurry
  7. temperaturewas cooled
  8. filtrationthe solid was collected by filtration
  9. washwas washed with acetone

Sources & evidence

ORD record
ord-982e4805e8a640ea94ee241afc2e2917
Source dataset
uspto-grants-1983_02
Patent number
US04374843

Reaction notes

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