Hydrochloric Acid → HCID 178488944, compound

HRID 1653811Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]#[N:28])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[N-:29]=[N+:30]=[N-:31].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]3[NH:31][N:30]=[N:29][N:28]=3)[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 105 °C

Procedure

The procedure is as in Example 1. A mixture of 3.4 g of 6-[4,5-Bis(4-methoxyphenyl)-2-oxazolyl]hexanenitrile, 1.45 g of sodium azide and 1.76 g of ammonium chloride in 70 cm3 of dimethylformamide is heated to 105° C. for 60 hours. After the addition of sodium azide and ammonium chloride (in the same quantities as before), the mixture is brought again to 105° C. for 60 hours. At room temperature, the mixture is diluted with 210 cm3 of water, acidified with 2N hydrochloric acid and extracted with ethyl acetate (3 times 50 cm3), and the reaction product is purified as described in Example 1. The solid isolated is recrystallised in 60 cm3 of ethyl acetate, and 1.7 g (44.8%) of 5-{5-[4,5-bis(4-methoxyphenyl)-2-oxazolyl]pentyl}tetrazole, a white solid, melting point 150° C. are obtained.

Workup

extractionextracted with ethyl acetate (3 times 50 cm3)
customthe reaction product is purified
customThe solid isolated
customis recrystallised in 60 cm3 of ethyl acetate

Sources & evidence

ORD record: ord-6190d8e2c3e9429b817ded985394f8a3
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05403852

Reaction notes

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