Hydrochloric Acid → HCID 178441193, compound

HRID 1073233Notes

Reaction equation

HRID 1073233 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])([CH3:4])([CH3:3])[CH3:2].[Cl-].C([NH+](CC)CC)C.[N-:31]=[N+:32]=[N-:33].[Na+].Cl>O.CN1CCCC1=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:33][N:32]=[N:31][N:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 19987804HCID 19987804, compound

Product 1

HCID 178441193HCID 178441193, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Under a nitrogen atmosphere, a mixture of 7.00 g (0.023 mole) of 5-(3,5-di-t-butyl-4-hydroxyphenoxy)-valeronitrile, 4.73 g (0.034 mole) of triethylammonium chloride, 4,47 g (0.069 mole) of sodium azide and 200 ml of 1-methylpyrrolidone was heated at 150° C. for about 60 hours. The reaction mixture was cooled and then poured into 200 ml of water. The aqueous mixture was acidified to pH 1 with 10% hydrochloric acid and then extracted five times with 100 ml portions of diethyl ether. The diethyl ether extracts were combined, washed with brine, dried over magnesium sulfate and evaporated to provide an oil. The oil was purified by silica gel chromatography eluting with 2:1 hexane:acetone containing 3 ml of acetic acid per 1600 ml of solvent followed by recrystallization of the isolated material from a mixture of ethyl acetate and hexane to provide 3.3 g of 5-[4-(3,5-di-t-butyl-4-hydroxyphenoxy)butyl]tetrazole as a white solid, m.p. 141°-141.5° C. Analysis: Calculated for C19H30N4O2 : %C, 65.9; %H, 8.7; %N, 16.2; Found: %C, 65.7; %H, 8.6; %N, 16.2.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted five times with 100 ml portions of diethyl ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto provide an oil
  7. customThe oil was purified by silica gel chromatography
  8. washeluting with 2:1 hexane
  9. customacetone containing 3 ml of acetic acid per 1600 ml of solvent followed by recrystallization of the isolated material from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5b364cf0a5d54036b48991411c616154
Source dataset
uspto-grants-1990_11
Patent number
US04968710

Reaction notes

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