Methane → HCID 9838279, compound

HRID 1589152Notes

Reaction equation

HRID 1589152 reaction equation
[CH3:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2([C:16]([S:18]C)=S)[CH2:14][CH2:13][CH2:12][CH2:11][S:10]2=[O:15])[CH:4]=1.C>C(O)C.C(#N)C>[CH3:1][NH:2][C:16]([C:9]1([C:5]2[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11][S:10]1=[O:15])=[S:18]

Participants

6

Reactant 3

HCID 297MethaneHCID 6329Methylamine2×HCID 11011568HCID 11011568, compound

Product 1

HCID 9838279HCID 9838279, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
22 °C

Procedure

A 33% (weight/volume) solution of methylamine in ethanol (10.2 cc) is added dropwise, in the course of 5 minutes, to a solution of methyl 2-(pyridin-3-yl)tetrahydrothiopyran-2-carbodithioate 1-oxide (a single stereoisomeric form; 10.2 g) in ethanol (150 cc), kept at between 25° and 30° C. The solution is then stirred for 1 hour and 35 minutes at a temperature of about 22° C. and a further amount of 33% (weight/volume) solution of methylamine in ethanol (1.5 cc) is then added. After it has been stirred for 1 hour at the same temperature, the reaction mixture is concentrated to dryness under reduced pressure (25 mm Hg; 3.4 kPa) at 40° C. The product obtained (9.8 g) is dissolved in acetonitrile (15 cc) at a temperature of about 20° C. and the solution is kept at a temperature of about 5° C. for 1 hour. The resulting crystals are filtered off, washed twice with acetonitrile (10 cc in total) and dried under reduced pressure (25 mm Hg; 3.4 kPa) at 20° C. The product obtained (3.4. g), to which 0.8 g prepared under the same conditions has been added, is dissolved in boiling acetonitrile (80 cc); the solution is treated with decolourising charcoal (0.1 g) and filtered hot and the filtrate is then cooled at a temperature of about 5° C. for 2 hours. The resulting crystals are filtered off, washed twice with acetonitrile (10 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C. This gives the A form of N-methyl-2-(pyridin-3-yl)tetrahydrothiopyran-2-carbothioamide 1-oxide (3.3 g) melting at 228° C. [Rf=0.22 (chromatography on a thin layer of silica gel; solvent: ethyl acetate/methanol (80/20 by volume)].

Workup

  1. customkept at between 25° and 30° C
  2. stirringAfter it has been stirred for 1 hour at the same temperature
  3. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (25 mm Hg; 3.4 kPa) at 40° C
  4. customThe product obtained (9.8 g)
  5. waitthe solution is kept at a temperature of about 5° C. for 1 hour
  6. filtrationThe resulting crystals are filtered off
  7. washwashed twice with acetonitrile (10 cc in total)
  8. customdried under reduced pressure (25 mm Hg; 3.4 kPa) at 20° C
  9. customThe product obtained (3.4. g)
  10. customto which 0.8 g prepared under the same conditions
  11. additionhas been added
  12. dissolutionis dissolved
  13. filtrationfiltered hot
  14. temperaturethe filtrate is then cooled at a temperature of about 5° C. for 2 hours
  15. filtrationThe resulting crystals are filtered off
  16. washwashed twice with acetonitrile (10 cc in total)
  17. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C

Sources & evidence

ORD record
ord-6001b4d75e00486993fb9dd21e9f39d8
Source dataset
uspto-grants-1986_02
Patent number
US04568682

Reaction notes

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