Dimethylamine → HCID 20434281, compound

HRID 1154697

Reaction equation

HRID 1154697 reaction equation
[SH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].C[O-].[Na+].Cl[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26]Cl)[N:21]=1.[CH3:28][NH:29][CH3:30]>CO.C(Cl)Cl>[CH3:28][N:29]([CH2:19][C:20]1[N:21]=[C:22]([CH2:26][S:1][CH2:2][CH2:3][N:4]2[C:8](=[O:9])[C:7]3=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]3[C:5]2=[O:14])[CH:23]=[CH:24][CH:25]=1)[CH3:30]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962482-PhthalimidoethanethiolHCID 3166542,6-Bis(chloromethyl)pyridineHCID 10942334Sodium Methoxide

Product 1

HCID 20434281HCID 20434281, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-mercaptoethyl) phthalimide (28.8 g, 0.139 mol) in dry methanol (250 ml) is added sodium methoxide (7.5 g, 0.139 mol) with cooling and stirring. This mercaptide solution is added to 2,6-bis(chloromethyl)pyridine (24.5 g, 0.139 mol) in dry methanol (250 ml). The mixture is stirred at room temperature for 21/2 hours and is filtered to remove the precipitated solid. Then dimethylamine (6.9 g, 0.153 mol) in cold methanol (150 ml) is added to the filtrate and the mixture is stirred at room temperature overnight. The solvent is removed in vacuo leaving an amber gum. The gum is taken up in methylene chloride (200 ml) and is washed with aqueous sodium bicarbonate and with water. The methylene chloride layer is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This gives 24.3 g of 6-dimethylaminomethyl-2-[(2-phthalimidoethyl)thiomethyl]pyridine as a crude amber gum.

Workup

  1. temperaturewith cooling
  2. stirringThe mixture is stirred at room temperature for 21/2 hours
  3. filtrationis filtered
  4. customto remove the precipitated solid
  5. stirringthe mixture is stirred at room temperature overnight
  6. customThe solvent is removed in vacuo
  7. customleaving an amber gum
  8. washis washed with aqueous sodium bicarbonate and with water
  9. dry with materialThe methylene chloride layer is dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68ae5f5889ee49be83fb4a3600db0820
Source dataset
uspto-grants-1984_12
Patent number
US04490533

Linked notes

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