Acetonitrile → HCID 18937922, compound

HRID 357605Notes

Reaction equation

HRID 357605 reaction equation
[NH2:1][C:2]1[N:3]([N:14]=CC2C=CC=CC=2)[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:6]=1.O.NN.C(#N)C>C(O)COCCO>[NH2:14][N:3]1[CH:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:6]=[C:2]1[NH2:1]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24654Hydrazine hydrate (1:1)HCID 53836347HCID 53836347, compound

Product 1

HCID 18937922HCID 18937922, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5.3 g (0.0189 mol) of 2-amino-1-benzylideneamino-4-(4-fluorophenyl)-imidazole and 12.5 ml of hydrazine hydrate in 18.8 ml of diethylene glycol is stirred at 140° C. for 15 hours. After cooling to 80° C., 70 ml of acetonitrile are added to the reaction mixture, which is then cooled further to 0° C. The product that has separated out is filtered off and washed with acetonitrile and diethyl ether. In that manner there is obtained the title compound, m.p. 227°-230° C., 1H-NMR (DMSO): δ=7.57-7.68 (m, 2H); 7.06-7.15 (m, 2H); 7.01 (s, 1H); 5.52 (s, 2H); 5.36 (s, 2H).

Workup

  1. temperatureis then cooled further to 0° C
  2. customThe product that has separated out
  3. filtrationis filtered off
  4. washwashed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-4a857a51c1a54ff0b4a5af7e0eaa03a6
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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