Hydrochloric Acid → HCID 178444961, compound

HRID 1609295Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:31])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:19]=1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[NH:32]1[C:1]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:31])[C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:22][CH:23]=2)=[N:2][N:34]=[N:33]1

Participants

Conditions

Temperature: 120 °C

Procedure

In 20 ml of DMF was dissolved 1.20 g of N-[2-(2-cyanophenylthio)phenyl]-4-hexyloxybenzamide followed by addition of 0.36 g of sodium azide and 0.30 g of ammonium chloride, and the mixture was stirred at 120° C. for 3 hours. Then, the same amounts of sodium azide and ammonium chloride as above were added twice at an interval of 3 hours. The reaction mixture was then acidified with diluted hydrochloric acid and the resulting crystals were collected by filtration and washed with water. The crystals were dissolved in chloroform and dried over magnesium sulfate and the solvent was distilled off. The crystals thus obtained were recrystallized from ethyl acetate-n-hexane to give 1.1 g of the title compound as white crystals, m.p. 154°-156° C.

Workup

filtrationthe resulting crystals were collected by filtration
washwashed with water
dissolutionThe crystals were dissolved in chloroform
dry with materialdried over magnesium sulfate
distillationthe solvent was distilled off
customThe crystals thus obtained
customwere recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record: ord-dcb5d43cc08442988e90d318e06d6363
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05399703

Reaction notes

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