Hydrochloric Acid → HCID 178441194, compound

HRID 1073228Notes

Reaction equation

HRID 1073228 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
  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-49392baf9edc446a920cd97113a91017
Source dataset
uspto-grants-1990_11
Patent number
US04968710

Reaction notes

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