Water → HCID 178488114, compound

HRID 2370307Notes

Reaction equation

HRID 2370307 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20]Br)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8]([S:10][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[N:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7721p-Xylyl bromideHCID 10796Cesium carbonateHCID 178488032HCID 178488032, compound

Product 1

HCID 178488114HCID 178488114, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-methoxy-2-mercaptobenzimidazole (1.673 g, 9.285 mmol) and p-xylyl bromide (1.718 g, 9.285 mmol) in DMF (33.5 mL) at 0° C., Cs2CO3 (4.53 g, 13.93 mmol) was added and the suspension was stirred for 24 h while being allow to warm from 0° C. to rt. Distilled water (150 mL) was added with vigorous stirring. The murky white suspension turned into a clearer solution with white granules. After being stirred for 20 min at rt, the mixture was filtered and the residue was rinsed with water (3×20 mL) and hexanes (3×20 mL). The crude product was >95% pure by 1H NMR analysis and was not further purified. The yield was 2.437 g, 92%. 1H NMR (500 MHz, CDCl3): δ 2.25 (s, 3H), 3.76/3.78 (app d*, 3H), 4.38/4.42 (app d*, 2H), 6.74-7.17 (m, 6H), 7.52 (d, 1H, J=7.5 Hz), 8.87 (brs, 1H); 13C NMR (125 MHz, CDCl3): δ 21.30, 37.39, 37.63, 55.89, 55.96, 94.15, 101.18, 110.39, 111.10, 112.45, 119.07, 128.98, 129.58, 133.94, 156.61. *The apparent doublets may arise from the 1,3-proton shift between the nitrogen atoms in the heterocycle.

Workup

  1. temperatureto warm from 0° C. to rt
  2. stirringAfter being stirred for 20 min at rt
  3. filtrationthe mixture was filtered
  4. washthe residue was rinsed with water (3×20 mL) and hexanes (3×20 mL)

Sources & evidence

ORD record
ord-43a8da8813824252bccc22bd59c9e50c
Source dataset
uspto-grants-2014_04
Patent number
US08710082B2

Reaction notes

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