Ammonium Chloride → HCID 178441187, compound

HRID 1073225Notes

Reaction equation

HRID 1073225 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>O.CN(C)C=O>[C:1]([C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=1[OH:25])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[NH:28][N:27]=[N:26][N:20]=2)=[CH:17][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 15027730HCID 15027730, compound

Product 1

HCID 178441187HCID 178441187, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.68 g (5 mmole) of 2,6-di-t-butyl-4[(4-cyanophenyl)methoxy]phenol (from Example 1) 0.97 g (15 mmole) of sodium azide, 0.30 g (15 mmole) of ammonium chloride, 0.21 g (5 mmole) of lithium chloride and 25 ml of N,N-dimethylformamide was heated in a stoppered flask at 100° C. for 16 hours. The reaction mixture was poured into a mixture of ice and water, and was then extracted with chloroform. The chloroform extract was washed with water, dried and evaporated to give the crude product as an oil. The oil was triturated with water to give a solid. The solid was purified by silica gel chromatography eluting with a mixture of methanol/chloroform/acetic acid in a ratio of 5/94.5/0.5 followed by two recrystallizations from a mixture of methanol, chloroform and hexane to give 0.22 g of white 5-[4-(3,5-di-t-butyl-4-hydroxyphenoxymethyl)phenyl]tetrazole, m.p. 235°-237° C. Analysis: Calculated for C22H28N4O2 : %C, 69.4; %H, 7.4; %N, 14.7; Found: %C, 69.0; %H, 7.6; %N, 14.6.

Workup

  1. extractionwas then extracted with chloroform
  2. extractionThe chloroform extract
  3. washwas washed with water
  4. customdried
  5. customevaporated
  6. customto give the crude product as an oil
  7. customThe oil was triturated with water
  8. customto give a solid
  9. customThe solid was purified by silica gel chromatography
  10. washeluting with a mixture of methanol/chloroform/acetic acid in a ratio of 5/94.5/0.5
  11. customfollowed by two recrystallizations from a mixture of methanol, chloroform and hexane

Sources & evidence

ORD record
ord-6dcbb5cad26a46fd8d3c6edd358540df
Source dataset
uspto-grants-1990_11
Patent number
US04968710

Reaction notes

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