N-Methylbenzeneethanamine → HCID 20244136, compound

HRID 482885Notes

Reaction equation

HRID 482885 reaction equation
C(=O)(O)[O-].[K+].[CH3:6][NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:16][C:17]1[C:18](=[O:23])[S:19][S:20][C:21]=1Cl>CO>[Cl:16][C:17]1[C:18](=[O:23])[S:19][S:20][C:21]=1[N:7]([CH3:6])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11503N-MethylbenzeneethanamineHCID 145034,5-Dichloro-3H-1,2-dithiol-3-oneHCID 516893Potassium Bicarbonate

Product 1

HCID 20244136HCID 20244136, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

Potassium bicarbonate (6 g) and a solution of N-methylphenethylamine (8 g) in methanol (150 cc) are added to a solution of 4,5-dichloro-1,2-dithiol-3-one (11.2 g) in methanol (350 cc). The reaction mixture is stirred at a temperature of about 20° C. for 20 hours, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue is dissolved in methylene chloride (210 cc); the solution obtained is washed 3 times with distilled water (60 cc in total), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The crystals obtained are recrystallized from a mixture of isopropyl ether and ethyl acetate (75/25 by volume); 4-chloro-5-[N-methyl-N-(2-phenylethyl)-amino]-1,2-dithiol-3-one (5.3 g) is thus obtained in the form of yellow crystals of m.p. 75° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  3. dissolutionThe residue is dissolved in methylene chloride (210 cc)
  4. customthe solution obtained
  5. washis washed 3 times with distilled water (60 cc in total)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  9. customThe crystals obtained
  10. customare recrystallized from a mixture of isopropyl ether and ethyl acetate (75/25 by volume)

Sources & evidence

ORD record
ord-fb27a00c8c4e485288bcabba51598fa4
Source dataset
uspto-grants-1986_03
Patent number
US04576954

Reaction notes

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