Methyl iodide → HCID 66692138, compound

HRID 1048976Notes

Reaction equation

HRID 1048976 reaction equation
[CH3:1][S:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]([OH:16])[C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[N:9][C:5]=2[CH:4]=1.[CH2:19]1COCC1.CI>>[CH3:19][O:16][N:7]1[C:6]2[CH:17]=[CH:18][C:3]([S:2][CH3:1])=[CH:4][C:5]=2[N:9]=[C:8]1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 66692195HCID 66692195, compound

Product 1

HCID 66692138HCID 66692138, compound

Procedure

To a stirred solution of 5-(methyl-thio)-2-(pyridin-3-yl)-1H-benzo[d]imidazol-1-ol (0.36 g, 0.001 mol) in THF (20 ml) NaH (60% suspension in mineral oil), (0.14 g, 0.003 mol) was added. After stirring for the next 20 min at room temperature methyl iodide (0.39 g, 0.002 mol) was added drop wise. The resulting solution was continued to stir at room temperature for the next 3 h. The reaction was quenched with ice cold water and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated under vacuum to afford to afford the crude compound which was purified by chromatography to obtain title compound 1-methoxy-5-(methyl-thio)-2-(pyridin-3-yl)-1H-benzo[ ]imidazole as a stick brown solid. 1H NMR (400 MHz, DMSO-d6), δ 9.47 (s, 1H), 8.74-8.73 (m, 1H), 8.53-8.50 (m, 1H), 7.71 (s, 1H), 7.49-7.33 (m, 3H), 4.05 (s, 3H) 2.58 (s, 3H). MS (M+1): 272.

Workup

  1. additionwas added drop wise
  2. customThe reaction was quenched with ice cold water
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customto afford
  8. customto afford the crude compound which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-16fd269d4f65487a9793df26fe47183b
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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