Hydrochloric Acid → HCID 178441131, compound

HRID 36728Notes

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])[NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])([CH3:4])([CH3:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-].[NH4+].[Cl-].[Li+].Cl>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])[NH:8][C:9]1[CH:10]=[C:11]([C:12]2[NH:27][N:26]=[N:25][N:13]=2)[CH:14]=[CH:15][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

Eight g (0.025 mole) of 3-(3,5-di-t-butyl-4-hydroxyanilino)benzonitrile (from Example 27), 4.9 g (0.075 mole) of sodium azide, 4.0 g (0.075 mole) of ammonium chloride, 1.06 g (0.025 mole) of lithium chloride and 60 ml of N,N-dimethylformamide were combined under a nitrogen atmosphere and heated at 110° C. for 48 hours. The reaction mixture was poured into cold 6N hydrochloric acid and a gummy solid precipitated out. The supernatant was decanted off and the residue dissolved in ethanol. The ethanol solution was diluted with water and a pink solid was collected. This material was recrystallized from a mixture of ethanol and water to give 5.97 g of 5-[3-(3,5-di-t-butyl-4-hydroxyanilino)phenyl]tetrazole, m.p. 231°-233° C. Analysis: Calculated for C21H27N5O: % C, 69.0; % H, 7.4; % N, 19.2; Found: % C, 68.4; % H, 7.6; % N, 18.8.

Workup

customa gummy solid precipitated out
customThe supernatant was decanted off
dissolutionthe residue dissolved in ethanol
additionThe ethanol solution was diluted with water
customa pink solid was collected
customThis material was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record: ord-c2dca49cb3a5440daf23bf3a3ea12d31
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05416113

Reaction notes

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