Hydrochloric Acid → HCID 178446927, compound

HRID 231565Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH+:6]1C=CC=C[CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:17]=[CH:18][C:19]([NH:21][C:22]1[C:27]2[O:28][CH2:29][CH2:30][O:31][C:26]=2[CH:25]=[CH:24][CH:23]=1)=[O:20].Cl>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:17]=[CH:18][C:19]([NH:21][C:22]1[C:27]2[O:28][CH:29]([C:7]3[NH:6][N:3]=[N:2][N:1]=3)[CH2:30][O:31][C:26]=2[CH:25]=[CH:24][CH:23]=1)=[O:20]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium azide (490 mg) and pyridinium chloride (870 mg) were added to a solution of 8-(3-methoxy-4-pentyloxycinnamoyl)amino-1,4-benzodioxane (560 mg; synthesized in reference example 2) in dry dimethylformamide (3 ml). In an atmosphere of argon, the solution was stirred for 1.5 hrs at 100° C. The reaction solution cooled to room temperature was poured into 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried, and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (390 mg) having the following physical data:

Workup

temperatureThe reaction solution cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materiala saturated aqueous solution of sodium chloride, dried
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-f371f86a8e05479b8d93623cdd559b66
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04847275

Reaction notes

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