Aluminium lithium hydride → HCID 86606567, compound

HRID 2244420Notes

Reaction equation

HRID 2244420 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[S:15][C:14]([CH3:16])=[N:13][C:12]=2[C:17](=[O:26])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:25][C:21]1[CH:20]=[C:19]([NH:18][C:17]([C:12]2[N:13]=[C:14]([CH3:16])[S:15][C:11]=2[NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=2)=[O:26])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68405811HCID 68405811, compound

Product 1

HCID 86606567HCID 86606567, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[4-(3-chloro-phenylcarbamoyl)-2-methyl-thiazol-5-ylamino]-benzoic acid methyl ester (0.02 g, 0.05 mmol) in THF (1.00 ml) was treated at room temperature with lithium aluminium hydride (0.008 g, 0.20 mmol) and stirred at room temperature for 30 min. The reaction mixture was quenched with a drop of 5N NaOH and sodium sulphate. The solids were filtered and the mother liquor evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate) to yield the title compound (0.02 g, 90%) as a light brown gum.

Workup

  1. customThe reaction mixture was quenched with a drop of 5N NaOH and sodium sulphate
  2. filtrationThe solids were filtered
  3. customthe mother liquor evaporated
  4. customThe residue was purified by flash chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-0f5ffe7018164383b8c99f06710dc94d
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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