Acetic Acid → {2-Butyl-4-chloro-1-[(4-nitrophenyl)methyl]-1H-imidazol-5-yl}acetic acid

HRID 653865Notes

Reaction equation

HRID 653865 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[C:7](CC#N)=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].Cl.[C:25]([OH:28])(=[O:27])[CH3:26]>>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[C:7]([CH2:26][C:25]([OH:28])=[O:27])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 15159733HCID 15159733, compound

Product 1

HCID 15356444{2-Butyl-4-chloro-1-[(4-nitrophenyl)methyl]-1H-imidazol-5-yl}acetic acid

Procedure

2-Butyl-4-chloro-5-(cyanomethyl)-1-(4-nitrobenzyl)imidazole (7.08 g) and a 1:1 mixture of 12N HCl and glacial acetic acid (175 mL) were mixed and refluxed for 6 hours. The solvents were removed by rotary evaporation and water (300 mL) was then added to the residue. After a few minutes, the product precipitated and was collected and dried to give 7.35 g of a solid; m.p. 207.0°-210.0°. NMR (200 MHz, DMSO-d6 /CDCl3) δ 8.20 (d, 2H, J=10Hz); 7.22 (d, 2H, J=10Hz); 5.28 (s, 2H); 3.42 (s, 2H); 2.52 (t, 2H, J=7Hz); 1.64 (m, 2H); 1.34 (m, 2H); 0.86 (t, 3H, J=7Hz). Anal. Calcd. for C16H18ClN3O4 ; C, 54.63; H, 5.16; N, 11.84. Found: C, 54.52; H, 5.05; N, 12.21.

Workup

  1. additionwere mixed
  2. temperaturerefluxed for 6 hours
  3. customThe solvents were removed by rotary evaporation and water (300 mL)
  4. additionwas then added to the residue
  5. waitAfter a few minutes
  6. customthe product precipitated
  7. customwas collected
  8. customdried

Sources & evidence

ORD record
ord-3d93f6e82f314ae5afc8935b26c5c831
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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