Aluminum(III) Chloride → HCID 5272001, compound

HRID 1072015Notes

Reaction equation

HRID 1072015 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[N:11]1([CH2:20][C:21]2[N:25]([CH2:26][C:27]([NH:29][CH3:30])=O)[C:24]3[CH:31]=[CH:32][CH:33]=[CH:34][C:23]=3[N:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1>O1CCCC1>[N:11]1([CH2:20][C:21]2[N:25]([CH2:26][CH2:27][NH:29][CH3:30])[C:24]3[CH:31]=[CH:32][CH:33]=[CH:34][C:23]=3[N:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 6481624HCID 6481624, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 5272001HCID 5272001, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an oven dried round bottom flask, lithium aluminum hydride (26 mg, 0.69 mmol) and aluminum chloride (97 mg, 0.73 mmol) were stirred in 10 mL of anhydrous tetrahydrofuran at 70-80° C. for 1 hour. 2-(2-Benzotriazol-1-ylmethyl-1-H-benzimidazol-1-yl)-N-methyl acetamide (50 mg, 0.156 mmol) was added. After 3 hours, more lithium aluminum hydride (1 M in tetrahydrofuran, 0.312 mL, 0.312 mmol) was added. The reaction mixture was allowed to stirred for 2 additional hours. The solvent was evaporated, and the residue was purified by flash chromatography (CH2Cl2/MeOH=15:1) to give 14 mg (28%) of the title compound as an oil.

Workup

  1. customIn an oven dried round bottom flask
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography (CH2Cl2/MeOH=15:1)

Sources & evidence

ORD record
ord-4e0d9f06a50348e8bbcbf3aa94f7d56d
Source dataset
uspto-grants-2005_06
Patent number
US06908936B2

Reaction notes

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