Ammonia → HCID 21942422, compound
Reaction equation
[OH:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=3)[O:12][N:11]=2)=[N:8][CH:9]=1)=O.C(Cl)(=O)C(Cl)=O.[Cl-].[NH4+].[N:30]1C=CC=CC=1.N>ClCCl>[NH2:30][C:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=3)[O:12][N:11]=2)=[N:8][CH:9]=1)=[O:1]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-(5-hydroxycarbonylpyrid-2-yl)-5-(3-bromophenyl)-1,2,4-oxadiazole (269.4 mg, 0.78 mmol) in dichloromethane (15 mL) was treated with 2M oxalyl chloride (0.90 mL, 1.8 mmol, dichloromethane) and a catalytic amount N,N-dimethylformaide. The resulting mixture was stirred at ambient temperature for 1.5 hours and the solvent and excess oxalyl chloride removed, in vacuo. The acid chloride in dichloromethane (5 mL) was then treated with solid ammonium chloride (450 mg, 8.4 mmol) and pyridine (1.5 mL, 18.5 mmol). The mixture was stirred vigorously at ambient temperature for 15 hours, and then treated with 2M ammonia (5 mL, 10 mmol, methanol). The solvent was then removed in vacuo, and the residue treated with water. Collection of the precipitate by filtration afforded crude 3-(5-aminocarbonylpyrid-2-yl)-5-(3-bromophenyl)-1,2,4-oxadiazole.
Workup
- customthe solvent and excess oxalyl chloride removed, in vacuo
- stirringThe mixture was stirred vigorously at ambient temperature for 15 hours
- customThe solvent was then removed in vacuo
- additionthe residue treated with water
- customCollection of the precipitate
- filtrationby filtration
Sources & evidence
- ORD record
- ord-abe48a02de794477a53b1a843d12bef5
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07112595B2
Reaction notes
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