Sodium sulfate decahydrate → HCID 68763541, compound

HRID 1398927Notes

Reaction equation

HRID 1398927 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]([OH:36])[C:16]1[N:20]([CH2:21][CH2:22][C:23](OC)=[O:24])[C:19]2[C:27]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:28][CH:29]=[CH:30][C:18]=2[N:17]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]([OH:36])[C:16]1[N:20]([CH2:21][CH2:22][CH2:23][OH:24])[C:19]2[C:27]([N:31]([CH2:32][CH3:33])[CH2:34][CH3:35])=[CH:28][CH:29]=[CH:30][C:18]=2[N:17]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 68772648HCID 68772648, compound

Product 1

HCID 68763541HCID 68763541, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (327 mg, 8.61 mmol) in tetrahydrofuran (38 mL) was added a solution of methyl 3-{2-[(2,4-dichlorophenyl)(hydroxy)methyl]-7-(diethylamino)-1H-benzimidazol-1-yl}propanoate (2.00 g, 4.31 mmol) in tetrahydrofuran (5 mL) at −5° C. After the addition, sodium sulfate decahydrate (3.3 g) was added. After 1 h, the resultant mixture was filtrated and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (1.42 g, 3.36 mmol, 78%).

Workup

  1. additionwas added
  2. filtrationthe resultant mixture was filtrated
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with a 30-70% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-b77b24ba8dcd40f9b98f5dd8ccf0eb1c
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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