Sodium sulfate decahydrate → HCID 67146660, compound

HRID 2422238Notes

Reaction equation

HRID 2422238 reaction equation
[CH3:1][N:2]([CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=1)[C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][N:2]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:23][CH:24]=1)[C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21273587HCID 21273587, compoundHCID 67147049HCID 67147049, compound

Product 1

HCID 67146660HCID 67146660, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, to a solution of methyl 4-[[methyl(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzoate (2.06 g, 6.1 mmol) in tetrahydrofuran (30 mL) was added 0.9 M diisobutylaluminum hydride-hexane solution (30 mL, 27 mmol). The reaction mixture was stirred at room temperature for 2 hrs, sodium sulfate 10 hydrate (8.7 g, 27 mmol) was added and the mixture was stirred at room temperature for 1 hr. Insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) to give the title compound (1.9 g, yield 98%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c9e14047e1234a7fb4a61aaecf53b1cd
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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