Sodium Methoxide → 1-benzyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 602564Notes

Reaction equation

HRID 602564 reaction equation
[Cl-].[CH2:2]([N+:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]2[C:18]([CH3:21])=[CH:19][S:20][C:10]=12)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:22][O-:23].[Na+]>CO>[CH2:2]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11](/[C:18](/[CH3:21])=[CH:19]\[S:20][CH3:10])[C:22]1=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866417049-Benzyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride

Product 1

HCID 462035751-benzyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-oneYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg of 9-benzyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride (0.635 mmol) were solubilised in methanol (25 mL), then 137 mg of NaOMe (4 eq) were added and the solution stirred at room temperature. After 48 h the solvent was evaporated, water was added (20 mL) and the mixture extracted with CH2Cl2 (3×20 mL). The organic layer was dried with MgSO4 and evaporated under reduced pressure. The residue was then purified by chromatography on silica gel (eluent: CH2Cl2) to afford 1-benzyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one as a colourless oil (186 mg, 94% yield). 1H NMR (300 MHz, CDCl3) δH 2.18 (3H, d, J=1.1, CH3), 2.26 (3H, s, SCH3), 5.10 (3H, s, NCH2), 6.27 (1H, q, J=1.1, H5), 6.84-7.10 (4H, m, arom), 7.25-7.35 (5H, m, arom); 13C NMR (75 MHz, CDCl3) δC 16.90, 20.44, 44.79, 108.50, 109.00, 121.24, 121.48, 126.61, 127.37, 127.57 (2C), 127.65, 127.69, 128.69 (2C), 129.45, 136.22, 152.34; HRMS m/z calcd C18H19N2OS [M+H]+: 311.1212; found: 311.1211.

Workup

  1. customAfter 48 h the solvent was evaporated
  2. additionwater was added (20 mL)
  3. extractionthe mixture extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe organic layer was dried with MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was then purified by chromatography on silica gel (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-cc175c1eb51b4988b32cab185fd2db19
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

Loading…