1-Bromo-2-butanone → 2-Amino-1-benzylideneamino-4-ethyl-imidazole

HRID 357608Notes

Reaction equation

HRID 357608 reaction equation
[C:1]([NH:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[NH:3])[NH2:2].Br[CH2:14][C:15](=O)[CH2:16][CH3:17]>C(O)C>[NH2:3][C:1]1[N:4]([N:5]=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:14]=[C:15]([CH2:16][CH3:17])[N:2]=1

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 178513139HCID 178513139, compound

Product 1

HCID 544586492-Amino-1-benzylideneamino-4-ethyl-imidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.62 g (0.01 mol) of benzaldehyde guanylhydrazone and 0.84 g (0.005 mol) of 1-bromo-2-butanone (Aldrich, Buchs, Switzerland; tech. 90%, Cat. no. 24,329-9) in 5 ml of ethanol is stirred for one hour in an ice-water bath and for 16 hours at 20° C. The reaction mixture is then concentrated to dryness by evaporation. The residue is taken up in lethyl acetate, washed twice with water and once with dilute sodium chloride solution, and dried over MgSO4. The ethyl acetate solution is concentrated, whereupon the title compound crystallizes out, m.p. 164°-167° C., 1H-NMR (DMSO): δ=8.41 (s, 1H); 8.89 (m, 2H); 7.46 (m, 3H); 7.13 (s, 1H); 5.9 (s, 2H); 2.34 (q, 2H); 1.13 (t, 3H).

Workup

  1. concentrationThe reaction mixture is then concentrated to dryness by evaporation
  2. washwashed twice with water and once with dilute sodium chloride solution
  3. dry with materialdried over MgSO4
  4. concentrationThe ethyl acetate solution is concentrated, whereupon the title compound
  5. customcrystallizes out

Sources & evidence

ORD record
ord-7c0c4efd390347cb95d8b58c40d7d1c5
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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