Hydrazine hydrate (1:1) → HCID 67500002, compound

HRID 1502580Notes

Reaction equation

HRID 1502580 reaction equation
[Cl:1][C:2]1[N:3](/[N:13]=C/C2C=CC(Cl)=CC=2)[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1.O.NN>COCCO>[Cl:1][C:2]1[N:3]([NH2:13])[CH:4]=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 87423121HCID 87423121, compound

Product 1

HCID 67500002HCID 67500002, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of E-2-Chloro-N-(4-chlorobenzylidene)-4-(pyridin-3-yl)-1H-imidazol-1-amine (210 mg, 0.66 mmol) in 2-methoxyethanol (5 mL) was added 80% hydrazine hydrate (0.5 mL). The reaction mixture was heated to 130° C. for 1 hour and then the reaction mixture was concentrated. The residue was purified by column chromatography (petroleum ether: ethyl acetate=1:1) to give the title compound (100 mg, 78%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.91 (s, 1H), 8.50-8.49 (m, 1H), 8.06-8.03 (m, 1H), 7.43 (s, 1H), 7.34-7.30 (m, 1H), 4.87 (br, 2H); ESIMS m/z 195 [(M+H)]+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by column chromatography (petroleum ether: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-1bd5d2f8336a4c5b81006f1fc8051148
Source dataset
uspto-grants-2015_12
Patent number
US09210931B2

Reaction notes

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