Ammonium Chloride → HCID 178423942, compound

HRID 890676Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium azide (4.12 g) and 2.97 g of ammonium chloride were added to 27 ml of a solution of 2.70 g of 2-methyl-2-{6-[5-methyl-2-(p-tolyl)oxazol-4-yl]hexyloxy}-propiononitrile in N,N-dimethylformamide, and stirred for 1.5 hours at 120° C. To the reaction solution was added ice-cold water, and extracted with ethyl acetate, washed with water and brine sequentially, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform:methanol=100:1 to 50:1) and recrystallized from isopropyl ether to provide 1.69 g of the objective compound as colorless crystals. M.p. 87° C.

Workup

additionTo the reaction solution was added ice-cold water
extractionextracted with ethyl acetate
washwashed with water and brine sequentially
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform:methanol=100:1 to 50:1)
customrecrystallized from isopropyl ether

Sources & evidence

ORD record: ord-08a502733c18402485ce7d629ea137af
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06998412B2

Reaction notes

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