Epichlorohydrin → HCID 18765666, compound

HRID 731156Notes

Reaction equation

HRID 731156 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(N(C(C)C)CC)(C)C.[CH2:15]([CH:17]1[O:19][CH2:18]1)[Cl:16]>C(#N)C>[N:1]1[N:2]([CH2:18][CH:17]([OH:19])[CH2:15][Cl:16])[N:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 81531DiisopropylethylamineHCID 178418441HCID 178418441, compound

Product 1

HCID 18765666HCID 18765666, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.905 g of tetrazole (100 mmol) and 1.75 ml of diisopropylethylamine (10 mmol) and 11.73 ml of epichlorohydrine (150 mmol) in anhydrous acetonitrile (30 ml) was stirred at 60° C. for 4 hours. The obtained solution was evaporated, dried on highvac and purified on a column of silica in chloroform-methanol 100:8. The first fraction provided pure 3-(2-H-tetrazol-2-yl)-2-hydroxy-1-chloropropane, 6.215 g (colorless oil, 38% Y), the second fraction yielded 9.208 g of pure 3-(1-H-tetrazol-1-yl)]-2-hydroxyl-1-chloropropane (sticky gum; 57% Y).

Workup

  1. customThe obtained solution was evaporated
  2. customdried on highvac and
  3. custompurified on a column of silica in chloroform-methanol 100:8

Sources & evidence

ORD record
ord-79df19bd9c004e9792e5adb9d58b06b8
Source dataset
uspto-grants-2009_09
Patent number
US07582756B2

Reaction notes

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