Ammonium Chloride → HCID 178439648, compound

HRID 653078Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

1-[2-Hydroxy-3-propyl-4-(4-cyanomethylphenylmethoxy)phenyl]ethanone (4.25 g; 0.013 m) was dissolved in dry dimethylformamide (70 ml) to which was added sodium azide (3.42 g; 0.052 m) and ammonium chloride (1.4 g; 0.026 m). The resulting suspension was heated at 100° C. for 20 hours with stirring under a capillary air condenser. The cooled suspension was poured onto water with stirring, acidified and filtered to give a pale brown solid. The solid was taken up in aqueous sodium hydroxide (2N), washed with chloroform and acidified with concentrated hydrochloric acid with cooling and stirring, filtered to give a pale brown solid. Recrystallised from methanol to give a fawn crystalline solid m.p. 184°-187° C.

Workup

additionThe cooled suspension was poured onto water
stirringwith stirring
filtrationfiltered
customto give a pale brown solid
washwashed with chloroform
temperaturewith cooling
stirringstirring
filtrationfiltered
customto give a pale brown solid
customRecrystallised from methanol

Sources & evidence

ORD record: ord-ad0b8227918e4f8899f5b7ba8d5e0f0d
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04675334

Reaction notes

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