Hydrochloric Acid → HCID 178441194, compound

HRID 974102Notes

Reaction equation

HRID 974102 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])([CH3:4])([CH3:3])[CH3:2].[Cl-].C([NH+](CC)CC)C.[N-:32]=[N+:33]=[N-:34].[Na+].Cl>O.CN1CCCC1=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[NH:34][N:33]=[N:32][N:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 19987806HCID 19987806, compound

Product 1

HCID 178441194HCID 178441194, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Under a nitrogen atmosphere, a mixture of 3.79 g (0.012 mole) of 6-(3,5-di-t-butyl-4-hydroxyphenoxy)hexanenitrile, 2.45 g (0.018 mole) of triethylammonium chloride, 2.31 g (0.036 mole) of sodium azide and 150 ml of N-methylpyrrolidinone was heated at about 150° C. for about 72 hours. The reaction mixture was cooled and poured into water. The aqueous mixture was acidified to pH 1 with 10% hydrochloric acid and then extracted six times with 100 ml portions of diethyl ether The diethyl ether extracts were combined, dried over magnesium sulfate and evaporated to provide a yellow oil. This oil was purified by silica gel chromatography eluting with 2:1 hexane:acetone containing 3 drops of acetic acid per 2000 ml of solvent, followed by recrystallization from a mixture of ethyl acetate and hexane to provide 2.2 g of 5-[5-(3,5-di-t-butyl-4-hydroxyphenoxy)pentyl]tetrazole as an off-white crystalline solid, m.p. 140°-141° C. Analysis: Calculated for C20H32N4O2 : %C, 66.6; %H, 8.95; %N, 15.5; Found: %C, 66.5; %H, 8.9; %N, 15.6.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted six times with 100 ml portions of diethyl ether The diethyl ether extracts
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto provide a yellow oil
  6. customThis oil was purified by silica gel chromatography
  7. washeluting with 2:1 hexane
  8. customacetone containing 3 drops of acetic acid per 2000 ml of solvent, followed by recrystallization from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-bb2add170b3043518173e8c47392c1c8
Source dataset
uspto-grants-1991_11
Patent number
US05066822

Reaction notes

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