Hydrochloric Acid → HCID 178441191, compound

HRID 974101Notes

Reaction equation

HRID 974101 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])[O:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])([CH3:4])([CH3:3])[CH3:2].[Cl-].C([NH+](CC)CC)C.[N-:30]=[N+:31]=[N-:32].[Na+].Cl>O.CN1CCCC1=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])[O:8][CH2:9][CH2:10][CH2:11][C:12]1[NH:32][N:31]=[N:30][N:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 15027734HCID 15027734, compound

Product 1

HCID 178441191HCID 178441191, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Under a nitrogen atmosphere a mixture of 8.66 g (0.030 mole) of 4-(3,5-di-t-butyl-4-hydroxyphenoxy)butyronitrile, 6.42 g (0.047 mole) of triethylammonium chloride, 5.79 g (0.089 mole) of sodium azide and 250 ml of 1-methylpyrrolidinone was heated about 150° C. for about 72 hours. The reaction mixture was poured into water. The pH was adjusted to pH 1 with 10% hydrochloric acid and then the mixture was extracted eight times With 100 ml portions of diethyl ether. The diethyl ether extracts were combined, washed with brine, dried over magnesium sulfate and then evaporated to provide a yellow orange oil. The oil was purified by silica gel chromatography eluting with 2:1 hexane:acetone containing 3 ml of acetic acid per 2000 ml of solvent, followed by recrystallization from a mixture of ethyl acetate and hexane to provide 2.66 g of 5-[3-(3,5-di-t-butyl-4-hydroxyphenoxy)propyl]tetrazole as a white solid, m.p. 179°-180° C. Analysis: Calculated for C18H28N4O2 : %C, 65.0; %H, 8.5; %N, 16.8; Found: %C, 65.3; %H, 8.5; %N, 16.8.

Workup

  1. extractionthe mixture was extracted eight times With 100 ml portions of diethyl ether
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto provide a yellow orange oil
  6. customThe oil was purified by silica gel chromatography
  7. washeluting with 2:1 hexane
  8. customacetone containing 3 ml of acetic acid per 2000 ml of solvent, followed by recrystallization from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b88ae9a9426f4510bd11a6687551689e
Source dataset
uspto-grants-1991_11
Patent number
US05066822

Reaction notes

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