Hydrochloric Acid → HCID 78322693, compound
Reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][S:4][C:3]=1[C:13]([O:15]C)=O.C(N(CC)CC)C.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1.Cl>O1CCOCC1>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[C:13](=[O:15])[C:3]3[S:4][CH:5]=[C:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:2]=3[NH:1][C:32]2=[O:33])=[CH:27][CH:26]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
Methyl 3-amino-4-phenylthiophene-2-carboxylate (400 mg, 1.71 mmol), triethylamine (0.04 ml, 0.43 mmol), and 4-chlorophenyl isocyanate (0.39 ml, 3.16 mmol) were dissolved in 1,4-dioxane (10 ml) in a reaction vessel. The mixture was heated with stirring at 90° C. for 3 days. After the completion of the reaction was confirmed by TLC, the reaction mixture was cooled to room temperature and filtered. The filtered solid was dissolved in a 10% sodium hydroxide/methanol (3 ml/12 ml) solution and refluxed with stirring at 100° C. overnight. After completion of the reaction, the reaction solution was cooled to room temperature, acidified with 3 N hydrochloric acid, and filtered to give 548 mg (1.54 mmol, 90% yield) of the title compound as a solid.
Workup
- temperatureThe mixture was heated
- temperaturethe reaction mixture was cooled to room temperature
- filtrationfiltered
- dissolutionThe filtered solid was dissolved in a 10% sodium hydroxide/methanol (3 ml/12 ml) solution
- temperaturerefluxed
- stirringwith stirring at 100° C. overnight
- customAfter completion of the reaction
- temperaturethe reaction solution was cooled to room temperature
- filtrationfiltered
Sources & evidence
- ORD record
- ord-9daec66431bc4fb6a29dc33ad9c71fcb
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260448B2
Reaction notes
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