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

HRID 602571Notes

Reaction equation

HRID 602571 reaction equation
[I-].[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)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[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])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866417069-Heptyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide

Product 1

HCID 462039051-heptyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-oneYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

257 mg of 9-heptyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide (0.620 mmol) were solubilised in methanol (40 mL), then 268 mg (8 eq) of NaOMe 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 to afford 1-heptyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one as a pale green oil (164 mg, 83%). Rf=0.65 (CH2Cl2/AcOEt 8:2); 1H NMR (300 MHz, CDCl3) δ=0.82-0.87 (3H, m, CH3), 1.14-1.44 (8H, m, 4-CH2), 1.75 (2H, quint, J=7.1, CH2), 2.12 (3H, d, J=1.2, CH3), 2.21 (3H, s, SCH3), 3.86 (2H, t, J=7.3, CH2), 6.21 (1H, q, J=1.2, H5), 6.80-7.14 (4H, m, Ar). 13C NMR (75 MHz, CDCl3) δ=13.86, 16.67, 20.20, 22.34, 26.52, 28.07, 28.70, 31.49, 40.91, 107.64, 108.80, 120.69, 121.15, 126.53, 127.23, 127.39, 129.52, 151.96; HRMS m/z C18H27N2OS [M+H]+ calcd: 319.1839, found: 319.1838.

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

Sources & evidence

ORD record
ord-66e1cad48ba7481794bd935ddfe8f844
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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