Ethyl Acetate → HCID 59667596, compound

HRID 1621123Notes

Reaction equation

HRID 1621123 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:11][C:12]=1[CH3:13])(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+].C(OCC)(=O)C>CN(C=O)C>[N:20]([CH2:6][CH2:7][C:8]1[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:11][C:12]=1[CH3:13])=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 22087831HCID 22087831, compound

Product 1

HCID 59667596HCID 59667596, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a brown solution of 2-(5-methyl-2-phenylthiazol-4-yl)ethyl methanesulfonate (200 mg, 673 μmol; prepared according to WO 2001/021602) in DMF (2.5 mL) was added sodium azide (52.5 mg, 807 μmol) at RT. The mixture was heated to 60° C. and stirred for 3 h and was then allowed to slowly cool down to RT. The reaction mixture was poured into ethyl acetate (50 mL) and the organic phase was washed with water (3×25 mL) and brine (1×25 mL). The aqueous layers were back-extracted with ethyl acetate (1×50 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 174 mg crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as colorless oil (107 mg, 438 μmol, 65.1%).

Workup

  1. temperatureto slowly cool down to RT
  2. washthe organic phase was washed with water (3×25 mL) and brine (1×25 mL)
  3. extractionThe aqueous layers were back-extracted with ethyl acetate (1×50 mL)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff09138c0d8a45d292dbbdb86b02c0b4
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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