Sodium hydride → HCID 58437589, compound

HRID 2092403Notes

Reaction equation

HRID 2092403 reaction equation
[OH:1][CH2:2][C:3]1[S:7][CH:6]=[N:5][CH:4]=1.[H-].[Na+].F[C:11]1[CH:12]=[C:13]([CH3:20])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18]>CN(C=O)C>[CH3:20][C:13]1[CH:12]=[CH:11][C:16]([N+:17]([O-:19])=[O:18])=[C:15]([CH:14]=1)[O:1][CH2:2][C:3]1[S:7][CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 27632165-Thiazolylmethanol

Product 1

HCID 58437589HCID 58437589, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(hydroxymethyl)-1,3-thiazole (1 g, 8.68 mmol) in DMF (15 mL) was added NaH (0.413 g, 9.47 mmol) under an argon atmosphere. The reaction mixture was stirred for 20 min at 0° C. 3-Fluoro-4-nitrotoluene (1.2 g, 7.89 mmol) was added. The resulting mixture was stirred for 1 h at RT, quenched by addition of a saturated aqueous solution of NaHCO3 and extracted with AcOEt. The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2; hexane/AcOEt 60:40→40:60) to afford 936 mg of the title compound as an orange solid. TLC: RF=0.35 (hexane/AcOEt 1:1); HPLC: LtRet=4.26 min; LC-MS: m/z 251.2 [M+H]+.

Workup

  1. stirringThe resulting mixture was stirred for 1 h at RT
  2. customquenched by addition of a saturated aqueous solution of NaHCO3
  3. extractionextracted with AcOEt
  4. washThe organic phase was washed with a saturated aqueous solution of NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (SiO2; hexane/AcOEt 60:40→40:60)

Sources & evidence

ORD record
ord-35e7c29e54524b0c822a53d7409ab5a6
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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