Water → HCID 61375526, compound

HRID 2041138Notes

Reaction equation

HRID 2041138 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH3:8])[S:6][CH:7]=1.[N:9]([Si](C)(C)C)=[N+:10]=[N-:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[N:9]([CH2:2][C:3]1[N:4]=[C:5]([CH3:8])[S:6][CH:7]=1)=[N+:10]=[N-:11]

Participants

6

Reactant 4

HCID 962WaterHCID 78378AzidotrimethylsilaneHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 61375526HCID 61375526, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 4-(chloromethyl)-2-methyl-thiazole (350 mg, 2.37 mmol) and azidotrimethylsilane (315 μL, 2.37 mmol) in anhydrous THF (1 mL) under nitrogen. Add a 1M solution of tetrabutylammonium fluoride (3.6 mL, 3.56 mmol) in THF and stir at ambient temperature overnight. Pour the reaction mixture into water (10 mL), extract with ethyl ether (3×2 mL), wash the organic extracts with brine, thy over MgSO4, filter, and evaporate. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the desired intermediate as a colorless oil (165 mg, 45%).

Workup

  1. extractionextract with ethyl ether (3×2 mL)
  2. washwash the organic extracts with brine
  3. filtrationthy over MgSO4, filter
  4. customevaporate
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-edf7f8b331364e41a6d5b2d28b6ddc40
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

Loading…