Ammonium Chloride → HCID 178441222, compound

HRID 1073230Notes

Reaction equation

HRID 1073230 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([S: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]=1O)([CH3:4])([CH3:3])[CH3:2].[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].[Cl-].[Li+]>CN(C)C=O>[C:1]([C:5]1[CH:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[NH:28][N:27]=[N:26][N:20]=3)=[CH:15][CH:14]=2)[CH:8]=[C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 2314306HCID 2314306, compound

Product 1

HCID 178441222HCID 178441222, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2.0g (0.011 mole) of 2,6-di-t-butyl-4-[(4-cyanophenyl)methylthio]phenol, 1.1 g (0.034 mole) of sodium azide, 0.6 g (0.034 mole) of ammonium chloride, 0.24 g (0.011 mole) of lithium chloride and 20 ml of N,N-dimethylformamide was heated at 115° C. in a stoppered flask for 120 hours. The N,N-dimethylformamide was evaporated and the residual material partitioned between water and chloroform. The chloroform layer was dried with magnesium sulfate, and was then evaporated to give the crude product as a brown oil. This oil was purified by silica gel chromatography eluting with a mixture of chloroform/methanol/acetic acid in a ratio of 98/2/0.25 followed by two recrystallizations from a mixture of chloroform and hexane to give 0.92 g of 5-{4-[(3,5-di-t-butylphenylthio)methyl]phenyl}tetrazole as a cream-colored solid, m.p. 187°-189° C. Analysis: Calculated for C22H28N4OS: %C, 66.6; %H, 7.1; %N, 14.1; Found: %C, 66.6; %H, 7.3; %N, 14.3.

Workup

  1. customThe N,N-dimethylformamide was evaporated
  2. customthe residual material partitioned between water and chloroform
  3. dry with materialThe chloroform layer was dried with magnesium sulfate
  4. customwas then evaporated
  5. customto give the crude product as a brown oil
  6. customThis oil was purified by silica gel chromatography
  7. washeluting with a mixture of chloroform/methanol/acetic acid in a ratio of 98/2/0.25
  8. customfollowed by two recrystallizations from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-d4b746fbcf2d405eba4682eedadf5ffe
Source dataset
uspto-grants-1990_11
Patent number
US04968710

Reaction notes

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