Hydrochloric Acid → (3,4-Dihydro-2H-1-thia-4a,9-diaza-fluoren-6-yl)-methanol

HRID 638895Notes

Reaction equation

HRID 638895 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[CH2:16][CH2:17][CH2:18]Br.Cl.[OH-].[Na+]>C(O)C.CN(C=O)C>[S:12]1[C:10]2[N:11]([C:7]3[C:8]([N:9]=2)=[CH:13][CH:14]=[C:5]([CH2:3][OH:4])[CH:6]=3)[CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 12795323Methyl 2-sulfanylidene-2,3-dihydro-1H-benzimidazole-5-carboxylate

Product 1

HCID 22224508(3,4-Dihydro-2H-1-thia-4a,9-diaza-fluoren-6-yl)-methanolYield 69.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a round bottomed flask was added 4.06 grams of 2-Thioxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester, 4.04 grams of 1,3-dibromopropane 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 1M 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 concentrate yielded 3 grams (68%) product. NMR (DMSO): δ 7.91 (m, 3H), 4.13 (m, 2H), 3.93 (s, 1H), 3.23 (m, 2H, CH2), 2.48 (m, 2H, CH2). MS: 221.0 (M+H).

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
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-31643cdc08ab41028a264c4a1a27d2bd
Source dataset
uspto-grants-2010_04
Patent number
US07691842B2

Reaction notes

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