Triethylamine hydrochloride → HCID 178442551, compound

HRID 1653820Notes

Reaction equation

HRID 1653820 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([CH3:28])[C:26]#[N:27])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[N-:29]=[N+:30]=[N-:31].[Na+].Cl.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:26]3[NH:31][N:30]=[N:29][N:27]=3)[CH3:28])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 20080546HCID 20080546, compound

Product 1

HCID 178442551HCID 178442551, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.45 g of (RS)-7-[4,5-bis(4-chlorophenyl)-2-oxazolyl]-2-methylheptanenitrile in 40 cm3 of dimethylformamide are treated with twice 2.1 g of sodium azide and twice 4.4 g of triethylamine hydrochloride under the (time and temperature) conditions defined in Example 1. After treatment, the product of the reaction is chromatographed on a column 2.8 cm in diameter containing 115 g of silica gel (50 to 200μ). The column is eluted with 1.2 liters of diisopropyl ether and then with 2.8 liters of a diisopropyl ether/ethyl acetate (80:20 by volume) mixture, collecting 200 cm3 fractions. The fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa). 2.7 g (55%) of (RS)-5-{7-[4,5-bis(4-chlorophenyl)-2-oxazolyl]-2-heptyl}-1H-tetrazole are obtained in the form of white crystals, melting point 144° C.

Workup

  1. customAfter treatment, the product of the reaction is chromatographed on a column 2.8 cm in diameter
  2. additioncontaining 115 g of silica gel (50 to 200μ)
  3. washThe column is eluted with 1.2 liters of diisopropyl ether
  4. customwith 2.8 liters of a diisopropyl ether/ethyl acetate (80:20 by volume) mixture, collecting 200 cm3 fractions
  5. concentrationThe fractions from the last eluent mixture are concentrated to dryness under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-defdf1cdfae9476fb5b27d4ead5044d8
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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