Dimethylamine → 32577-97-2

HRID 1757244Notes

Reaction equation

HRID 1757244 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[S:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.CO.C(OCC)(=O)C.CCCCCC>[CH3:1][N:2]([CH3:3])[C:5]1[S:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1

Participants

8

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazole

Product 1

HCID 1898463532577-97-2

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of dimethylamine in ethanol (0.5 ml×33%) was added to a stirred suspension of 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole (540 mg)(J. Goerdeler, Chem. Ber. 1957, 90, p 182 or ICI EP 0006679) and potassium carbonate (1.0 g) in methanol. The solution was stirred at room temperature for three hours, and then the solvent removed under reduced pressure. The residue was taken up in ethyl acetate (40 ml), washed with water (20 ml) and brine (20 ml). The organic layers were dried (MgSO4), filtered and the solvent removed to afford a yellow gum. Flash chromatography using 10% ethyl acetate in hexane as eluent, afforded the product as a yellow oil (330 mg). 1H NMR (360 MHz, CDCl3) d 3.15 (6H, s, N(CH3)2), 4.51 (2H, s, Cl--CH2); MS (CI+) m/z 178 ((M+1)+, 95%).

Workup

  1. customthe solvent removed under reduced pressure
  2. washwashed with water (20 ml) and brine (20 ml)
  3. dry with materialThe organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed
  6. customto afford a yellow gum

Sources & evidence

ORD record
ord-c97bf548041c49fcab7c95b6c01d5283
Source dataset
uspto-grants-1995_08
Patent number
US05444074

Reaction notes

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