Ammonia → HCID 21942422, compound

HRID 431905Notes

Reaction equation

HRID 431905 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

7

Reactant 5

HCID 222AmmoniaHCID 1049PyridineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 21942609HCID 21942609, compound

Product 1

HCID 21942422HCID 21942422, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. customthe solvent and excess oxalyl chloride removed, in vacuo
  2. stirringThe mixture was stirred vigorously at ambient temperature for 15 hours
  3. customThe solvent was then removed in vacuo
  4. additionthe residue treated with water
  5. customCollection of the precipitate
  6. filtrationby filtration

Sources & evidence

ORD record
ord-1e853defd65a4bc4b6805d4e18ea92e6
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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