Sodium hydride → HCID 66692195, compound

HRID 1048975Notes

Reaction equation

HRID 1048975 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:17]([O-:19])=O)=[C:7]([CH:16]=1)[NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[H-].[Na+]>C1COCC1>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[N:17]([OH:19])[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[N:8][C:7]=2[CH:16]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 66684791HCID 66684791, compound

Product 1

HCID 66692195HCID 66692195, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-(methyl-thio)-2-nitro-N-(pyridin-3-ylmethyl) aniline (0.8 g, 0.002 mol) in THF (20 ml) was added NaH (60% suspension in mineral oil), (0.14 g, 0.006 mol) and the resulting solution was continued to stir at 60° C. for 8 h. The reaction was quenched with ice chips and extracted with dichloromethane (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 5-(methyl-thio)-2-(pyridin-3-yl)-1H-benzo[d]imidazol-1-ol as an off white solid. 1H NMR (400 MHz, DMSO-d6), δ: 12.28 (bs, 1H), 9.36 (s, 1H), 8.71-8.70 (m, 1H), 8.55-8.53 (d, J=8 1H), 7.62-7.59 (m, 2H), 7.52-7.50 (d, J=8 Hz, 1H), 7.28-7.26 (dd, J=1.2 Hz, J=8 Hz, 1H), 2.53 (s, 3H). MS (M+1): 258.

Workup

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

Sources & evidence

ORD record
ord-60b513bb0ea04434adc0c1480b4b71a5
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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