Aluminium lithium hydride → HCID 178491757, compound

HRID 1517384Notes

Reaction equation

HRID 1517384 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[NH:20][C:19]3[C:21]([C:25](OC)=[O:26])=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:29])[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:26][CH2:25][C:21]1[C:19]2[NH:20][C:16]([CH2:15][N:13]([CH3:14])[S:10]([C:6]3[C:5]([CH3:29])=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=3[CH3:9])(=[O:12])=[O:11])=[N:17][C:18]=2[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178497579HCID 178497579, compound

Product 1

HCID 178491757HCID 178491757, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-((4-methoxy-N,2,6-trimethylphenylsulfonamido)methyl)-1H-benzo[d]imidazole-7-carboxylate (2.40 mmol, 1.0 eq.) was added dropwise to a suspension of LAH (5.28 mmol, 2.2 eq.) in abs. THF (5 ml) under N2 at 0° C. When the addition had ended, the reaction mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was then quenched with THF/water (9:1; 3 ml), while cooling, and filtered over Celite. The filtrate was concentrated to dryness and the crude product was purified by column chromatography over silica gel to obtain the desired product. Yield: 75%

Workup

  1. customat 0° C
  2. additionWhen the addition
  3. customThe reaction mixture was then quenched with THF/water (9:1; 3 ml)
  4. temperaturewhile cooling
  5. filtrationfiltered over Celite
  6. concentrationThe filtrate was concentrated to dryness
  7. customthe crude product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-146955f6b5074d57b961b0953598f96b
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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