Hydrochloric Acid → HCID 68981248, compound

HRID 349446Notes

Reaction equation

HRID 349446 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16](Cl)=[O:17])=[N:9]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH2:16][OH:17])[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 713752243-{2-[(4-Methoxyphenyl)methyl]-2H-tetrazol-5-yl}benzoyl chloride

Product 1

HCID 68981248HCID 68981248, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The acid chloride (2.5 g, 7.6 mmol) prepared in Step (d) of Example 1 was added to a suspension of lithium aluminum hydride (“LAH”) (0.58 g, 25 mmol) in tetrahydrofuran (10 mL) cooled to 0° C. The reaction mixture gradually warmed to room temperature over two hours. Aqueous HCl was added dropwise to quench excess LAH. The mixture was diluted with ethyl acetate and filtered through Celite. The filtrate was washed with brine, dried (MgSO4), and concentrated. The resulting viscous liquid was triturated with hexane/diethyl ether to yield a pale yellow solid (1.9 g, 84%). Mp 70–72° C.

Workup

  1. temperatureThe reaction mixture gradually warmed to room temperature over two hours
  2. customto quench excess LAH
  3. additionThe mixture was diluted with ethyl acetate
  4. filtrationfiltered through Celite
  5. washThe filtrate was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe resulting viscous liquid was triturated with hexane/diethyl ether

Sources & evidence

ORD record
ord-3ba93256fc114111a3a1065ffa32e713
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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