Triethylamine hydrochloride → HCID 178488945, compound

HRID 1653826Notes

Reaction equation

HRID 1653826 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]([CH3:31])([CH3:30])[C:28]#[N:29])[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-:32]=[N+:33]=[N-:34].[Na+].Cl.C(N(CC)CC)C>CN(C)C=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]([C:28]3[NH:34][N:33]=[N:32][N:29]=3)([CH3:31])[CH3:30])[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

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 20080522HCID 20080522, compound

Product 1

HCID 178488945HCID 178488945, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of 7-[4,5-bis(4-methoxyphenyl)-2-oxazolyl)-2,2-dimethylheptanenitrile in 12 cm3 of dimethylformamide are treated with twice 2.7 g of sodium azide and twice 4.95 g of triethylamine hydrochloride according to the (time and temperature) conditions defined in Example 1. After treatment, the product of the reaction is chromatographed on a column 3.5 cm in diameter containing 120 g of silica gel (50 to 200μ). The column is eluted, collecting 50 cm3 fractions, with 0.5 liter of diisopropyl ether and then with 1.3 liters of a diisopropyl ether/ethyl acetate (70:30 by volume) mixture. The fractions emerging at between 0.85 liter and 1.3 liters are concentrated under reduced pressure (0.2 kPa). The solid is taken up with 30 cm3 of diethyl ether and drained, washed with 10 cm3 of diethyl ether and dried. 2.8 g (50%) of 5-{7-[ 4,5-bis(4-methoxyphenyl)-2-oxazolyl]-2-methyl-2heptyl}-1H-tetrazole are obtained in the form of white crystals, melting point 82° C.

Workup

  1. customAfter treatment, the product of the reaction is chromatographed on a column 3.5 cm in diameter
  2. additioncontaining 120 g of silica gel (50 to 200μ)
  3. washThe column is eluted
  4. customcollecting 50 cm3 fractions
  5. concentrationare concentrated under reduced pressure (0.2 kPa)
  6. washwashed with 10 cm3 of diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-57b338b7736846b68a2ffaaa61f512ff
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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