Ammonium Chloride → HCID 178441192, compound

HRID 1074282Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture containing 2.87 g (0.10 mole) of 5-(3,5-di-t-butylphenoxy)pentanenitrile, 1.95 g (0.03 mole) sodium azide, 1.60 g (0.03 mole) ammonium chloride, 0.42 g (0.01 mole) lithium chloride and 25 ml of dimethylformamide was heated at 120° C. in a stoppered flask for about sixteen hours. Analysis of the reaction mixture by high pressure liquid chromatography revealed that the reaction still contained nitrile. The reaction was recharged with 1.95 g of sodium azide and 1.60 g of ammonium chloride and heated for an additional sixteen hours. The reaction mixture was poured into 250 ml of water. The resulting precipitate was collected, rinsed with water, air dried and recrystallized twice from aqueous methanol to give 1.8 g of white solid 5-[4-(3,5-di-t-butylphenoxy)butyl]tetrazole, m.p. 140°-141° C. Analysis: Calculated for C19H30N4O: %C, 69.1; %H, 9.2; %N, 17.0; Found: %C, 69.0; %H, 9.1; %N, 17.1.

Workup

temperatureheated for an additional sixteen hours
customThe resulting precipitate was collected
washrinsed with water, air
customdried
customrecrystallized twice from aqueous methanol

Sources & evidence

ORD record: ord-7ff238cf6ac94a3abcd9e7d66288d516
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04973731

Reaction notes

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