Ammonia → Methyl 3-carbamoyl-5-iodobenzoate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:14])[CH:13]=1)[C:8](O)=[O:9])=[O:4].[NH3:15]>S(Cl)(Cl)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([I:14])[CH:13]=1)[C:8]([NH2:15])=[O:9])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3-methoxycarbonyl-5-iodobenzoic acid (3 g, 10 mmol) in thionyl chloride (2 mL) was heated for 2 hours at 60° C. The reaction mixture was cooled and concentrated in vacuo. The intermediate acid chloride was then diluted with tetrahydrofuran (10 mL) and cooled to 0° C. The mixture was then treated with a solution of 2M ammonia (20 mL, 40 mmol, methanol) and the reaction stirred for 1 hour at 0° C. The mixture was then filtered and the solvent removed in vacuo. Recrystallization from methanol afforded 2.5 g (82%) of 3-methoxycarbonyl-5-iodobenzamide, as a white solid.
Workup
- temperatureThe reaction mixture was cooled
- concentrationconcentrated in vacuo
- additionThe intermediate acid chloride was then diluted with tetrahydrofuran (10 mL)
- filtrationThe mixture was then filtered
- customthe solvent removed in vacuo
- customRecrystallization from methanol
Sources & evidence
- ORD record
- ord-1f05c32e004d4355a32a89ebfd1eb798
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07112595B2
Reaction notes
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