Ethyl Acetate → 2-[5-(3-Methoxy-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-1H-benzoimidazole

HRID 732015Notes

Reaction equation

HRID 732015 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[SH:10].Cl[CH2:12][C:13]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)[O:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.CCCCCC>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([C:16]2[O:15][N:14]=[C:13]([CH2:12][S:10][C:2]3[NH:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:1]=3)[N:17]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 117155623-(Chloromethyl)-5-(3-methoxyphenyl)-1,2,4-oxadiazoleHCID 178527775HCID 178527775, compound

Product 1

HCID 98408012-[5-(3-Methoxy-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-1H-benzoimidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

1H-Benzoimidazole-2-thiol (150 mg, 1 mmol) was added to a solution of the 3-chloromethyl-5-(3-methoxy-phenyl)-[1,2,4]oxadiazole (30 mg, 0.13 mmol) and potassium carbonate (50 mg, 0.36 mmol) in DMF (2 ml) at room temperature. The solvent was removed in vacuo and the product obtained by flash chromatography using 20-100% ethyl acetate in hexane. 1H NMR (CDCl3), δ (ppm): 7.71 (d, 1H), 7.62 (d, 1H), 7.53 (m, 2H), 7.42 (t, 1H), 7.18 (overlapping, m, 3H), 4.52 (s, 2H), 3.87 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe product obtained by flash chromatography

Sources & evidence

ORD record
ord-7d6addcbd6194390a86ccacfa62cd9f9
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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