Sulfuryl chloride → HCID 178439678, compound

HRID 34977Notes

Reaction equation

HRID 34977 reaction equation
[CH2:1]([C:4]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[NH:15][N:14]=[N:13][N:12]=1)[CH2:2][CH3:3].S(Cl)([Cl:24])(=O)=O>O1CCCC1>[CH2:1]([C:4]1[C:19]([OH:20])=[C:18]([Cl:24])[CH:17]=[CH:16][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[NH:12][N:13]=[N:14][N:15]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178439672HCID 178439672, compound

Product 1

HCID 178439678HCID 178439678, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.38 g. of 5-[4-(2-propyl-3-hydroxyphenoxy)butyl]-tetrazole in 25 ml. of tetrahydrofuran was cooled to -10° C. by means of an external alcohol-ice bath. One millimole of sulfuryl chloride was slowly added and the reaction mixture was stirred for one hour. The mixture was evaporated under reduced pressure and the residue was triturated with diethyl ether. The ether was evaporated and the residue was purified by reverse phase high pressure liquid chromatography. The appropriate fractions provided 42 mg. of the desired title product plus 92 mg. of the 2-propyl-3-hydroxy-6-chlorophenoxy isomer and a small amount of the 2-propyl-3-hydroxy-4,6-dichlorophenoxy compound.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was triturated with diethyl ether
  3. customThe ether was evaporated
  4. customthe residue was purified by reverse phase high pressure liquid chromatography
  5. customThe appropriate fractions provided 42 mg

Sources & evidence

ORD record
ord-340c8fdaad77471d99b281f109e27b91
Source dataset
uspto-grants-1988_08
Patent number
US04764521

Reaction notes

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