Dichloromethane → HCID 19890949, compound

HRID 893635Notes

Reaction equation

HRID 893635 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][Se:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.[NH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C.[Cl:32]CCl>>[ClH:32].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][Se:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:13]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 100093-AminopyridineHCID 19890937HCID 19890937, compound

Product 1

HCID 19890949HCID 19890949, compound

Procedure

To a solution of 3 g (0.0103 mol) 2-(2-picolylseleno)benzoic acid (from Example 1) in 20 ml dichloromethane that has been cooled to -10° C. is added with stirring 1.32 g (0.0103 mol) chloromethylenedimethyliminium chloride, the mixture is then stirred at room temperature for 2 hours then a solution of 0.97 g (0.0103 mol) 3-aminopyridine and 2.32 g (0.023 mol) triethylamine in 20 ml dichloromethane are added dropwise with in 10 minutes and stirring is continued at room temperature for 14 hours, the reaction mixture is extracted with 50 ml water and the separated dichloromethane phase is dried and the solvent removed. The oily residue is treated with 50 ml 1 N HCl and filtered, it is then basified with NaOH (5%) and extracted twice with 50 ml portions of dichloromethane. The organic phase is dried over sodium sulfate and the solvent removed, the residue is dissolved in 40 ml 2-propanol and treated slowly with stirring with 15 ml 2-propanol/10% HCl when the hydrochloride crystallizes out. This is washed with 50 ml diethyl ether.

Workup

  1. additionis added
  2. stirringstirring
  3. waitis continued at room temperature for 14 hours
  4. extractionthe reaction mixture is extracted with 50 ml water
  5. dry with materialthe separated dichloromethane phase is dried
  6. customthe solvent removed
  7. additionThe oily residue is treated with 50 ml 1 N HCl
  8. filtrationfiltered
  9. extractionextracted twice with 50 ml portions of dichloromethane
  10. dry with materialThe organic phase is dried over sodium sulfate
  11. customthe solvent removed
  12. dissolutionthe residue is dissolved in 40 ml 2-propanol
  13. additiontreated slowly
  14. stirringwith stirring with 15 ml 2-propanol/10% HCl when the hydrochloride
  15. customcrystallizes out
  16. washThis is washed with 50 ml diethyl ether

Sources & evidence

ORD record
ord-7fb046ac66c143a2a0fe6e57cdf0af00
Source dataset
uspto-grants-1992_06
Patent number
US05126357

Reaction notes

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