4-Bromobenzaldehyde → HCID 178517971, compound

HRID 1967129Notes

Reaction equation

HRID 1967129 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[N:3]=[CH:2]1.[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[O:20]([C:22]#[N:23])[K].Cl.N1C=CC=CC=1.[N+:31]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)#[C-:32]>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[CH:16]([C:15]4[CH:18]=[CH:19][C:12]([Br:11])=[CH:13][CH:14]=4)[C:32](=[N:31][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[NH:23][C:22]3=[O:20])=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 707414-BromobenzaldehydeHCID 79129Cyclohexyl isocyanideHCID 10176127Pyridinium chlorideHCID 178418250HCID 178418250, compoundHCID 178507353HCID 178507353, compound

Product 1

HCID 178517971HCID 178517971, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1H-Benzoimidazol-5-ylamine (1 mmol) and 4-Bromobenzaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours 2 ml of a solution of KOCN (KSCN) (2 mmol) and Pyridinehydrochloride (2 mmol) in MeOH is added was added. Finally 3-Isocyano-cyclohexane (1 mmol) is added. The reaction was stirred at room temperature for 48 h. After evaporation of the solvent the residue was purified with chromatographic methods. Yield: 0.290 g (64%); mp: 205° C., 1H-NMR (500 MHz, DMSO-D6): 1.05-1.12 (m, 3H, CH2), 1.22-1.28 (m, 3H, CH2), 1.52-1.74 (m, 4H, CH2), 1.86-1.89 (m, 1H, CH2), 4.40 (s, br., 1H, NH), 5.98 (s, 1H, CH—N), 7.24 (d, 3J=8.6 Hz, 2H, Ar), 7.36 (d, 3J=6.6 Hz, 1H, Benzimid), 7.48 (d, 3J=8.6 Hz, 2H, Ar), 7.64 (s, br., 1H, NH), 8.04 (d, 3J=7.6 Hz, 1H. imidazole), 8.08 (s, 1H. imidazole), 12.31 (s, br., 1H, NH). MS m/z 452.3 (M+H)+, HPLC (254 nm): rt 2.95 min (100%)

Workup

  1. additionwas added
  2. customAfter evaporation of the solvent the residue
  3. customwas purified with chromatographic methods
  4. customrt 2.95 min (100%)

Sources & evidence

ORD record
ord-04d964903f844fb0b3753a50da881f72
Source dataset
uspto-grants-2013_04
Patent number
US08420684B2

Reaction notes

Loading…