Aluminum(III) Chloride → 5-Benzyl-3b,4,5,6,7,7a-hexahydro-1-thia-5-aza-cyclopenta[alpha]inden-8-one

HRID 30271Notes

Reaction equation

HRID 30271 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](Cl)=[O:15])[CH:10]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH:11]([C:14](=[O:15])[C:18]3[S:19][CH:20]=[CH:21][C:17]=32)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86229221HCID 86229221, compound

Product 1

HCID 597894415-Benzyl-3b,4,5,6,7,7a-hexahydro-1-thia-5-aza-cyclopenta[alpha]inden-8-oneYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from step e) (4.9 g, 13.8 mmol) in CH2Cl2 (21 ml) was added dropwise to a slurry of AlCl3 (5.51 g, 41.4 mmol) in CH2Cl2 (47 ml) at 22° C. After 45 minutes, the reaction mixture was poured into ice cold 2 M NaOH (100 ml) and extracted with CH2Cl2 (300 ml). The organic extract was dried (MgSO4), solvent evaporated in vacuo and residue purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 50% ethyl acetate) to give the subtitle compound (1.8 g, 46%). MS calculated for C17H17NOS+H 284, observed 284.

Workup

  1. extractionextracted with CH2Cl2 (300 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4), solvent
  4. customevaporated in vacuo and residue
  5. custompurified by silica-gel chromatography

Sources & evidence

ORD record
ord-05f724f274724475884e3bcbdae18533
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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