HCID 11139613, compound → HCID 18782164, compound

HRID 1420549Notes

Reaction equation

HRID 1420549 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11139613HCID 11139613, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18782164HCID 18782164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-Carboxyphenyl)-5-methylbenzimidazole (2 g, 0.079 mM) was dissolved in dry tetrahydrofuran (100 ml) and cooled to 0° C. Lithium aluminium hydride (7.9 ml, 1.0 M solution) was added dropwise over 10 minutes. After complete addition the reaction was heated to reflux for 4 hours. The reaction was cooled and quenched by addition of water (2 ml) and 2N sodium hydroxide (4 ml). The reaction was diluted with ethyl acetate and filtered through hyflo, washing with ethyl acetate. Dried over magnesium sulphate and evaporated (1.2 g). MS M+ 239.

Workup

  1. additionAfter complete addition the reaction
  2. temperaturewas heated
  3. temperatureto reflux for 4 hours
  4. temperatureThe reaction was cooled
  5. customquenched by addition of water (2 ml) and 2N sodium hydroxide (4 ml)
  6. additionThe reaction was diluted with ethyl acetate
  7. filtrationfiltered through hyflo
  8. washwashing with ethyl acetate
  9. dry with materialDried over magnesium sulphate
  10. customevaporated (1.2 g)

Sources & evidence

ORD record
ord-5512e3fd18b84bf191208f6bff00a7ac
Source dataset
uspto-grants-2000_06
Patent number
US06071909

Reaction notes

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