Methane → HCID 19890947, compound

HRID 893636Notes

Reaction equation

HRID 893636 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][Se:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:2]=1.C(N(CC)CC)C.[NH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.C.[Cl:33]CCl>O>[ClH:33].[ClH:33].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][Se:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[O:13])[CH:2]=1

Participants

7

Reactant 5

HCID 297MethaneHCID 17274-AminopyridineHCID 6344DichloromethaneHCID 8471TriethylamineHCID 19890939HCID 19890939, compound

Product 1

HCID 19890947HCID 19890947, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4 g (0.0132 mol) 2-(3-picolylseleno)benzoic acid (from Example 2) and 4.4 ml triethylamine in 40 ml dichloromethane, that has been cooled to 0° C., is added in one portion 3.5 g (0.0132 mol) bis(2-oxo-3-oxazolidinyl)-phoshoryl chloride. After 15 minutes 1.3 g (0.0138 mol) 4-aminopyridine is added and the mixture stirred at 0° C. for 3.5 hours. It is then extracted twice with 100 ml portions of water, the organic phase dried over sodium sulfate and the solvent removed. The residue is taken up in 60 ml 2-propanol and treated with 10 ml 15% HCl in 2-propanol. The solid product that results is dissolved in 50 ml H2O and treated with 1 g active charcoal, stirred at room temperature for 15 minutes and then filtered. Acetone is added dropwise to the filtrate until the solution remains turbid. The crystals that are formed are filtered off after 2 hours and dried.

Workup

  1. extractionIt is then extracted twice with 100 ml portions of water
  2. dry with materialthe organic phase dried over sodium sulfate
  3. customthe solvent removed
  4. additiontreated with 10 ml 15% HCl in 2-propanol
  5. customThe solid product that results
  6. stirringstirred at room temperature for 15 minutes
  7. filtrationfiltered
  8. additionAcetone is added dropwise to the filtrate until the solution
  9. customThe crystals that are formed
  10. filtrationare filtered off after 2 hours
  11. customdried

Sources & evidence

ORD record
ord-f5d1b81f45554433a6d86f6381dbf668
Source dataset
uspto-grants-1992_06
Patent number
US05126357

Reaction notes

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