Water → HCID 67146901, compound

HRID 2422204Notes

Reaction equation

HRID 2422204 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:17][N:18]([CH2:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1)[C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:23]=1.O>O1CCCC1>[CH3:17][N:18]([CH2:30][C:31]1[CH:32]=[CH:33][C:34](/[CH:35]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:37][CH:38]=1)[C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 85970834HCID 85970834, compound

Product 1

HCID 67146901HCID 67146901, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of ethyl diethylphosphonoacetate (0.81 g, 3.6 mmol) in tetrahydrofuran (10 mL) was added 60% sodium hydride (0.14 g, 3.4 mmol), and the mixture was stirred for 30 min. A solution of 4-[[methyl(4-phenyl-2-thiazolyl)amino]methyl]benzaldehyde (0.80 g, 2.6 mmol) in tetrahydrofuran (10 mL) was added dropwise. The mixture was stirred at room temperature for 3 hrs, water was added, and the mixture was extracted with ethyl acetate. The extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.96 g, yield 98%) as a powder.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1)

Sources & evidence

ORD record
ord-35b12e7b9c9a45c0adfbdb0be28f073f
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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