Benzyl Alcohol → HCID 46203576, compound

HRID 602565Notes

Reaction equation

HRID 602565 reaction equation
[I-].[CH3:2][C:3]1[N:10]2[C:6](=[N+:7]([CH3:15])[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[S:5][CH:4]=1.[OH-:16].[Na+].O.[CH2:19](O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([S:5]/[CH:4]=[C:3](/[N:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([CH3:15])[C:6]1=[O:16])\[CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:19]([S:5]/[CH:4]=[C:3](\[N:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([CH3:15])[C:6]1=[O:16])/[CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 14798Sodium HydroxideHCID 30775083,9-Dimethyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide

Product 2

HCID 46203576HCID 46203576, compoundHCID 46203577HCID 46203577, compound

Procedure

Stage B 167 mg of 3,9-dimethyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide (0.51 mmol) and 162 mg of NaOH (8 eq) were solubilised in benzyl alcohol (5 mL) and the solution stirred under reflux. After 48 h 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 a mixture 55/45 of 1-[(1E)-1-(benzylsulfanyl)prop-1-en-2-yl]-3-methyl-1,3-dihydro-2H-benz imidazol-2-one and 1-[(1Z)-1-(benzyl sulfanyl)prop-1-en-2-yl]-3-methyl-1,3-dihydro-2H-benzimidazol-2-one isomers as a colourless oil (127 mg, 81% overall yield). HRMS m/z calcd C18H19N2OS [M+H]+: 311.1212; found: 311.1215 (analysis on the isomer mixture). The two isomers were separated by preparative TLC (eluent: CHCl3, eluted three times).

Workup

  1. temperatureunder reflux
  2. extractionthe mixture extracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe organic layer was dried with MgSO4
  4. customevaporated under reduced pressure
  5. customThe residue was then purified by chromatography on silica gel (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-3703ee7fdab44119beeeadd3bc9f3bce
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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