Hydrochloric Acid → (2,3-Dihydro-benzo[4,5]imidazo[2,1-b]thiazol-7-yl)-methanol

HRID 1744974Notes

Reaction equation

HRID 1744974 reaction equation
CO[C:3]([C:5]1[CH:14]=[CH:13][C:8]2[NH:9][C:10](=[S:12])[NH:11][C:7]=2[CH:6]=1)=[O:4].Br[CH:16](Br)[CH3:17].Cl.[OH-].[Na+]>C(O)C.CN(C=O)C>[S:12]1[CH2:17][CH2:16][N:9]2[C:8]3[CH:13]=[CH:14][C:5]([CH2:3][OH:4])=[CH:6][C:7]=3[N:11]=[C:10]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 112011,1-DibromoethaneHCID 14798Sodium HydroxideHCID 12795323Methyl 2-sulfanylidene-2,3-dihydro-1H-benzimidazole-5-carboxylate

Product 1

HCID 22224490(2,3-Dihydro-benzo[4,5]imidazo[2,1-b]thiazol-7-yl)-methanolYield 72.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a round bottomed flask was added 2.83 grams of 2-Thioxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester, 2.55 grams of dibromoethane and 50 ml DMF and 50 ml ethanol. The mixture was refluxed for 10 hours. Then it was concentrated to dry on a rotary evaporator. The solid was next dissolved in 100 ml THF and 20 ml of 1 M LiAlH4 (in THF) was next injected within five minutes. The reaction media was stirred at room temperature for one hour. Ethanol was next added (˜10 ml), followed by 50 ml 2N HCl. The aqueous layer was adjusted to basic Ph=14 with 10N sodium hydroxide. The aqueous was extracted with 2×500 ml ethyl acetate. The combined organic layers was dried over magnesium sulfate. Filter off the drying agent and cocentrate yielded 2.04 grams (60%) product. MS: 207.0 (M+H). H-NMR(DMSO): □ 7.34(m, 2H), 7.08 (m, 1H), 5.15(m, 1H, OH), 4.53 (m, 2H, CH2), 4.34 (m, 2H, CH2), 4.00 (m, 2H, CH2).

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. concentrationThen it was concentrated
  3. customto dry on a rotary evaporator
  4. dissolutionThe solid was next dissolved in 100 ml THF
  5. customThe reaction media
  6. extractionThe aqueous was extracted with 2×500 ml ethyl acetate
  7. dry with materialThe combined organic layers was dried over magnesium sulfate
  8. filtrationFilter off the drying agent and cocentrate

Sources & evidence

ORD record
ord-d0a92cd23b634f6c99cab642a5583d31
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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