Ammonium Chloride → HCID 178441195, compound

HRID 974100Notes

Reaction equation

HRID 974100 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])([CH3:4])([CH3:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>O.CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[NH:27][N:26]=[N:25][N:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 433294Lithium ChlorideHCID 19987808HCID 19987808, compound

Product 1

HCID 178441195HCID 178441195, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4.0 g (12.1 mmole) of 7-(3,5-di-t-butyl-4-hydroxyphenoxy)heptanenitrile (from Example 3), 2.35 g (36.2 mmole) sodium azide, 1.94 g (36.2 mmole) of ammonium chloride, 0.51 g (12.1 mmole) of lithium chloride and 50 ml of N,N-dimethylformamide was heated in a stoppered flask at 120° C. for 48 hours. To this mixture was added 2.35 g (36.2 mmole) of sodium azide and 1.94 g (36.2 mmole) of ammonium chloride, and heating was continued for an additional 48 hours. The reaction mixture was poured into water and extracted twice with chloroform. The chloroform extracts were combined, washed with water, dried with magnesium sulfate and evaporated to give the crude product as a dark oil. This oil was purified by four recrystallizations from a mixture of ethyl acetate and hexane, followed by silica gel chromatography eluting with a mixture of chloroform/methanol/acetic acid in a ratio of 98/2/0.25. After three further recrystallizations, 0.92 g of 5-[6-(3,5-di-t-butyl-4-hydroxyphenoxy)hexyl]-tetrazole, m.p. 128°-131° C., was obtained as a white solid. Analysis: Calculated for: C21H34N4O2 : %C, 67.4; %H, 9.2; %N, I5.0; Found %C, 67.4; %H, 9.3; %N, 15.2.

Workup

  1. temperatureheating
  2. extractionextracted twice with chloroform
  3. washwashed with water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-24a5771aface4fc39755dddcd16ab030
Source dataset
uspto-grants-1991_11
Patent number
US05066822

Reaction notes

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