Triethylamine → HCID 19896626, compound

HRID 1196865Notes

Reaction equation

HRID 1196865 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][CH:4]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>C(Cl)Cl.CCOCC.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].C(OCC)(=O)C>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:23]=[N+:24]=[N-:25])=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 592968[4-(Methylsulfanyl)phenyl]methanol

Product 1

HCID 19896626HCID 19896626, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A cold (5° C.) solution of 4-methylthiobenzyl alcohol (3.0 g, 19.45 mmol) in CH2Cl2 (60 mL) was treated with triethylamine (2.17 g, 21.4 mmol) and methanesulfonyl chloride (2.45 g, 21.4 mmol). The mixture was stirred for 1 h, then diluted with Et2O and filtered. The filtrate was evaporated to dryness, redissolved in CH3CN and treated with NaN3 (1.52 g, 23.34 mmol) and (Bu)4NCl (0.150 g). The mixture was stirred at room temperature for 18 h, then diluted with ethyl acetate and washed successively with water, dilute NaHCO3 and brine, dried (MgSO4), and finally evaporated. The crude compound was purified by silica gel chromatography (eluted with petroleum ether and CH2Cl2) to afford 2.79 g (80.0%) of the title product as a mobile oil.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to dryness
  3. dissolutionredissolved in CH3CN
  4. stirringThe mixture was stirred at room temperature for 18 h
  5. washwashed successively with water, dilute NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. customfinally evaporated
  8. customThe crude compound was purified by silica gel chromatography (eluted with petroleum ether and CH2Cl2)

Sources & evidence

ORD record
ord-2068725be4544d5faccc9e4da9bc27d6
Source dataset
uspto-grants-1992_05
Patent number
US05116833

Reaction notes

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