Methane → HCID 13711417, compound

HRID 2118719Notes

Reaction equation

HRID 2118719 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2([C:14]([S:16]C)=S)[S:13][CH2:12][CH2:11][CH2:10][S:9]2)[CH:5]=[CH:4][CH:3]=1.[CH3:18][NH2:19].C(OCC)(=O)C.C>C(O)C>[CH3:18][NH:19][C:14]([C:8]1([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)[S:13][CH2:12][CH2:11][CH2:10][S:9]1)=[S:16]

Participants

6

Reactant 4

HCID 297MethaneHCID 6329MethylamineHCID 8857Ethyl AcetateHCID 54535882HCID 54535882, compound

Product 1

HCID 13711417HCID 13711417, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of methyl 2-(6-methyl-2-pyridyl)-1,3-dithiane-2-carbodithioate (130.5 g) in 1.2 liters of ethanol maintained at a temperature in the region of 20° C., a 33% (weight/volume) solution (840 cc) of methylamine in ethanol is added dropwise in the course of 10 minutes. The mixture is then stirred for 4 hours at the same temperature. The crystals which appear are separated by filtration, washed twice with ethyl acetate (100 cc in total), 4 times with isopropyl ether (400 cc in total) and dried under reduced pressure (0.2 mm Hg; 0.03 kPa) at a temperature in the region of 20° C. The product thereby obtained (100.2 g), to which is added some product (18.4 g) prepared under the same conditions in a previous operation, is dissolved in boiling ethyl acetate (3.3 liters); to this solution is added decolorising charcoal (33 g), and the solution is filtered hot. The filter is washed 4 times with boiling ethyl acetate (400 cc in total). The filtrate and the washing liquors are combined and cooled for 4 hours to a temperature in the region of 0° C. The crystals which appear are separated by filtration, washed 4 times with ethyl acetate (200 cc in total, 6 times with isopropyl ether (600 cc in total), and then dried under reduced pressure (0.2 mm Hg; 0.03 kPa) at 55° C. N-Methyl-2-(6-methyl-2-pyridyl)-1,3-dithiane-2-carbothiamide (99.1 g), m.p. 168° C., is thereby obtained.

Workup

  1. customThe crystals which appear are separated by filtration
  2. washwashed twice with ethyl acetate (100 cc in total), 4 times with isopropyl ether (400 cc in total)
  3. customdried under reduced pressure (0.2 mm Hg; 0.03 kPa) at a temperature in the region of 20° C
  4. customThe product thereby obtained (100.2 g)
  5. customprepared under the same conditions in a previous operation
  6. dissolutionis dissolved
  7. additionto this solution is added
  8. filtrationthe solution is filtered hot
  9. washThe filter is washed 4 times with boiling ethyl acetate (400 cc in total)
  10. temperaturecooled for 4 hours to a temperature in the region of 0° C
  11. customThe crystals which appear are separated by filtration
  12. washwashed 4 times with ethyl acetate (200 cc in total, 6 times with isopropyl ether (600 cc in total)
  13. customdried under reduced pressure (0.2 mm Hg; 0.03 kPa) at 55° C

Sources & evidence

ORD record
ord-ecc5fe8867334832af61d760e722fdba
Source dataset
uspto-grants-1987_07
Patent number
US04680303

Reaction notes

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