Sodium Methoxide → HCID 46203907, compound

HRID 602578Notes

Reaction equation

HRID 602578 reaction equation
[I-].[CH3:2][C:3]1[N:10]2[C:6](=[N+:7]([CH3:19])[C:8]3[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:9]=32)[S:5][CH:4]=1.[CH3:20][O-:21].[Na+]>CO>[CH3:19][N:7]1[C:8]2[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:11][C:9]=2[N:10](/[C:3](/[CH3:2])=[CH:4]\[S:5][CH3:6])[C:20]1=[O:21]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86641708HCID 86641708, compound

Product 1

HCID 46203907HCID 46203907, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

90 mg (0.23 mmol) of 3,9-dimethyl-6-(trifluoromethyl)[1,3]thiazolo[3,2-a][3,1]benzimidazol-9-ium iodide 6a were solubilised in MeOH (20 mL). NaOMe was added (8 eq, 100 mg) and the solution stirred under reflux for 2 h. The solvent was then evaporated and water was added (15 mL). The resulting mixture was extracted 3×15 mL of CH2Cl2, the organic layer dried with MgSO4 and evaporated under reduced pressure to yield 1-methyl-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one 7a (58 mg, orange oil, 85%). 1H NMR (300 MHz, CDCl3) δ=2.14 (3H, d, J=1.2, CH3), 2.27 (3H, s, SCH3), 3.47 (3H, s, NCH3), 6.29 (1H, q, J=1.2, H5), 7.03-7.10 (2H, m, Ar), 7.38-7.42 (1H, m, Ar); 13C NMR (75 MHz, CDCl3) δ=16.90, 20.33, 27.36, 106.06 (q, J=4), 107.28, 119.02 (q, J=4), 123.69 (q, J=33), 124.55 (q, J=271), 125.83, 127.36, 128.53, 132.82, 152.50; HRMS m/z C13H14F3N2OS [M+H]+ calcd: 303.0773, found: 303.0775.

Workup

  1. temperatureunder reflux for 2 h
  2. customThe solvent was then evaporated
  3. additionwater was added (15 mL)
  4. extractionThe resulting mixture was extracted 3×15 mL of CH2Cl2
  5. dry with materialthe organic layer dried with MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-47f8423767644322a71e5c8d6d5e6e14
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

Loading…