Aluminum(III) Chloride → HCID 22276824, compound

HRID 1063888Notes

Reaction equation

HRID 1063888 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:11][C:12]1[S:16][C:15]([CH:17]2[S:23][CH2:22][CH2:21][NH:20][C:19](=O)[CH2:18]2)=[CH:14][CH:13]=1>C(OCC)C.C1COCC1>[Br:11][C:12]1[S:16][C:15]([CH:17]2[S:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 22276508HCID 22276508, compound

Product 1

HCID 22276824HCID 22276824, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (22.9 g) was added to a suspension of lithium aluminum hydride (19.5 g) in diethyl ether (400 ml) under ice-cooling and a nitrogen atmosphere, and the mixture was stirred for 20 minutes. After a suspension of 7-(5-bromo-2-thienyl)perhydro-1,4-thiazepin-5-one (75 g) in THF (500 ml) was added therein under the same condition, the reaction mixture was stirred at room temperature for 2 hours, poured into ice water and extracted with ethyl acetate (1500 ml). The extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford 7-(5-bromo-2-thienyl)perhydro-1,4-thiazepine (60.5 g) as a solid.

Workup

  1. temperaturecooling
  2. additionwas added
  3. stirringunder the same condition, the reaction mixture was stirred at room temperature for 2 hours
  4. extractionextracted with ethyl acetate (1500 ml)
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dbe4ed0dda4400d84fbfed6b62127de
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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