Sodium Methoxide → 1-[3,5-bis(trifluoromethyl)benzyl]-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 602569Notes

Reaction equation

HRID 602569 reaction equation
[Cl-].[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:7][N+:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]2[C:17]([CH3:20])=[CH:18][S:19][C:9]=12.[CH3:30][O-:31].[Na+]>CO>[F:26][C:24]([F:25])([F:27])[C:22]1[CH:21]=[C:6]([CH:5]=[C:4]([C:3]([F:29])([F:28])[F:2])[CH:23]=1)[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10](/[C:17](/[CH3:20])=[CH:18]\[S:19][CH3:9])[C:30]1=[O:31]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866417059-[3,5-Bis(trifluoromethyl)benzyl]-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride

Product 1

HCID 462039041-[3,5-bis(trifluoromethyl)benzyl]-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-oneYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

285 mg of 9-[3,5-bis(trifluoromethyl)benzyl]-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride (0.632 mmol) were solubilised in methanol (40 mL), then 274 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-[3,5-bis(trifluoromethyl)benzyl]-3-[(1Z)-1-(methylsulfanyl)prop-1-en-2-yl]-1,3-dihydro-2H-benzimidazol-2-one as a white powder (211 mg, 77%). Mp 148° C.; Rf=0.72 (CH2Cl2/AcOEt 8:2); 1H NMR (300 MHz, CDCl3) δ=2.18 (3H, d, J=1.1, CH3), 2.26 (3H, s, SCH3), 5.20 (2H, brs, CH2), 6.31 (1H, q, J=1.1, H5), 6.82-7.15 (4H, m, Ar), 7.75 (3H, brs, Ar); 13C NMR (75 MHz, CDCl3) δ=16.79, 20.45, 43.95, 107.84, 109.41, 121.88, 121.88 (1C, sept, J=3), 122.00, 123.07 (2C, q, J=272), 126.34, 127.50 (2C, q, J=3), 127.94, 128.36, 128.78, 132.17 (2C, q, J=34), 139.07, 152.19; HRMS m/z C20H17F6N2OS [M+H]+ calcd: 447.0960, found: 447.0959.

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-b4248ad2ac5e46fb884a704f004caf21
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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