Stannous chloride dihydrate → 1-(4-Aminobenzyl)-2-butyl-4,5-dicyanoimidazole

HRID 466390Notes

Reaction equation

HRID 466390 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:7]([C:12]#[N:13])=[C:8]([C:10]#[N:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].O.O.[Sn](Cl)Cl>C(O)C>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:6]2[C:7]([C:12]#[N:13])=[C:8]([C:10]#[N:11])[N:9]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 198153892-Butyl-4,5-dicyano-1-(4-nitrobenzyl)imidazole

Product 1

HCID 198153621-(4-Aminobenzyl)-2-butyl-4,5-dicyanoimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-butyl-4,5-dicyano-1-(4-nitrobenzyl)imidazole (2.00 g, 6.5 mmol, 1 eq), tin dichloride dihydrate (7.30 g, 32.3 mmol, 5 eq) and ethanol (13 mL) was stirred and heated at 70° for 50 minutes. The reaction was terminated by pouring the mixture onto ice and adjusting the pH to 8 with saturated aqueous NaHCO3. The aqueous mixture was extracted with ethyl acetate (3×100 mL) and the organic layers were dried (MgSO4) and concentrated to give a thick amber oil. This oil was flash chromatographed over silica gel in 75:25 to 70:30 hexane/ethyl acetate yielding 330 mg of yellow crystals; m.p. 99.0°-103.5°. NMR (200 MHz, CDCl3) δ 6.97 (d, 2H, J=10 Hz); 6.68 (d, 2H, J=10 Hz); 5.10 (s, 2H); 2.69 (t, 2H, J=7 Hz); 1.72 (t of t, 2H, J=7,7 Hz); 1.38 (t of q, 2H, J=7,7 Hz); 0.91 (t, 3H, J=7 Hz). Mass Calcd. for C16H17N5 : 279.1483. Found: 279.1489.

Workup

  1. temperatureheated at 70° for 50 minutes
  2. customThe reaction was terminated
  3. additionby pouring the mixture onto ice
  4. extractionThe aqueous mixture was extracted with ethyl acetate (3×100 mL)
  5. dry with materialthe organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customto give a thick amber oil
  8. customchromatographed over silica gel in 75:25 to 70:30 hexane/ethyl acetate yielding 330 mg of yellow crystals

Sources & evidence

ORD record
ord-df696eb174e54ab29bf4f9ca8437bc72
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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