Dimethylformamide → HCID 16128760, compound

HRID 547594Notes

Reaction equation

HRID 547594 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:18][N:19]([CH:21]=O)C.[C:23](Cl)(=O)[C:24](Cl)=O.[CH2:29](Cl)Cl>>[N:19]1[CH:21]=[CH:24][CH:23]=[C:29]([O:16][C:15]([C:13]2[N:12]=[CH:11][N:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH:14]=2)=[O:17])[CH:18]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 16128759HCID 16128759, compound

Product 1

HCID 16128760HCID 16128760, compoundYield 10%

Procedure

1-(3-Nitro-phenyl)-1H-imidazole-4-carboxylic acid 21 (0.1 g, 0.4 mmol) was suspended in CH2Cl2 (5 mL) and a drop of DMF (cat.) was added. Then oxalyl chloride (111 μL, 1.29 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The organic layer was removed by decantation and the remaining solid was washed twice with CH2Cl2. The solid was suspended in CH2Cl2 and 3-hydroxypyridine was added dropwise. The clear solution was stirred at room temperature for 2 h after which 1N NaOH (aq) was added and the layers were separated. Concentration of the organic layer followed by column chromatography on silica gel with 5% MeOH in CH2Cl2 afforded 14 mg (10%) of 22 as a white solid. HRMS (ESI+): m/z=310.268 [M+H]

Workup

  1. customThe organic layer was removed by decantation
  2. washthe remaining solid was washed twice with CH2Cl2
  3. addition3-hydroxypyridine was added dropwise
  4. stirringThe clear solution was stirred at room temperature for 2 h after which 1N NaOH (aq)
  5. additionwas added
  6. customthe layers were separated

Sources & evidence

ORD record
ord-26bf32b7e62e4fa7a25c99905f7ce315
Source dataset
uspto-grants-2011_05
Patent number
US07939556B2

Reaction notes

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