Sodium Hydroxide → [1-(2-Diethylamino-ethyl)-2-(4-ethoxy-benzyl)-1H-benzoimidazol-5-yl]-thiourea

HRID 2074451Notes

Reaction equation

HRID 2074451 reaction equation
[CH2:1]([N:3]([CH2:37][CH3:38])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([NH:15][C:16]([NH:18]C(=O)C3C=CC=CC=3)=[S:17])=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=1)[CH3:2].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:37]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([NH:15][C:16]([NH2:18])=[S:17])=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=1)[CH3:38]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 16037889N-(1-(2-(diethylamino)ethyl)-2-(4-ethoxybenzyl)-1H-benzo[d]-imidazol-5-ylcarbamothioyl)benzamide

Product 1

HCID 59799762[1-(2-Diethylamino-ethyl)-2-(4-ethoxy-benzyl)-1H-benzoimidazol-5-yl]-thiourea

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(1-(2-(diethylamino)ethyl)-2-(4-ethoxybenzyl)-1H-benzo[d]-imidazol-5-ylcarbamothioyl)benzamide 20 (272 mg, 0.513 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. 2M NaOH (0.513 mL, 1.026 mmol) added and the solution was heated to reflux for 6 hours and cooled to room temperature overnight. The solution was concentrated and the residue was partitioned between H2O and ethyl acetate, transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine (twice), dried over magnesium sulphate, filtered and concentrated to afford an off white solid which was slurried in hot ethyl acetate to yield white solid 21 [1-(2-Diethylamino-ethyl)-2-(4-ethoxy-benzyl)-1H-benzoimidazol-5-yl]-thiourea. Yield: 110 mg (50.3%). 1H NMR (DMSO) δ: 0.80 (t, 6H, J=7.1), 1.29 (t, 3H, J=7.0), 2.41 (q, 4H, J=7.0), 2.45-2.50 (m, 2H), 3.96 (q, 2H, J=6.9), 4.12 (t, 2H, J=6.7), 4.24 (s, 2H), 6.86 (d, 2H, J=8.6), 7.09 (dd, 1H, J=8.4, 1.5), 7.16 (d, 2H, J=8.7), 7.24 (br, 1-2H), 7.40 (d, 1H, J=8.5), 7.51 (s, 1H), 9.56 (s, 1H). MS (ESI): 426 (MH+, 100%)

Workup

  1. customfitted with an condenser
  2. temperaturethe solution was heated
  3. temperatureto reflux for 6 hours
  4. concentrationThe solution was concentrated
  5. customthe residue was partitioned between H2O and ethyl acetate
  6. customtransferred to a separatory funnel
  7. customthe organic layer collected
  8. extractionThe aqueous layer was further extracted with ethyl acetate
  9. washthe combined organic layers were washed with brine (twice),
  10. dry with materialdried over magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto afford an off white solid which

Sources & evidence

ORD record
ord-47149fda9958425fbcfdfac5e7cace93
Source dataset
uspto-grants-2011_04
Patent number
US07919510B2

Reaction notes

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