Methane → HCID 10376941, compound

HRID 1701880Notes

Reaction equation

HRID 1701880 reaction equation
[CH3:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2([C:14]([S:16]C)=S)[CH2:13][CH2:12][CH2:11][S:10]2)[CH:4]=1.C>C(O)C>[CH3:1][NH:2][C:14]([C:9]1([C:5]2[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=2)[CH2:13][CH2:12][CH2:11][S:10]1)=[S:16]

Participants

5

Reactant 3

HCID 297MethaneHCID 6329MethylamineHCID 13043956Methyl 2-(pyridin-3-yl)thiolane-2-carbodithioate

Product 1

HCID 10376941HCID 10376941, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
0 °C

Procedure

A 33% (weight/volume) solution of methylamine in ethanol (11 cc) is added dropwise, in the course of 5 minutes, to a solution of methyl 2-(pyrid-3-yl)-tetrahydrothiophen-2-carbodithioate (14.3 g) in ethanol (50 cc), kept at a temperature of about 20° C. The solution is subsequently stirred for 5 hours at the same temperature and then cooled to 0° C. The resulting crystals are filtered off, washed with ethanol (8 cc) and then twice with diisopropyl ether (20 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. The product thus obtained (7.2 g) is dissolved in boiling ethanol (35 cc); decolourising charcoal (0.4 g) is added to the solution, which is filtered hot, and the filtrate is then cooled for 1 hour at a temperature of about 5° C. The resulting crystals are filtered off, washed with ethanol (5 cc) and then twice with diisopropyl ether (14 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C. N-Methyl-2-(pyrid-3-yl)-tetrahydrothiophen-2-carbothioamide (5.8 g), melting at 133° C., is thus obtained.

Workup

  1. customkept at a temperature of about 20° C
  2. filtrationThe resulting crystals are filtered off
  3. washwashed with ethanol (8 cc)
  4. dry with materialtwice with diisopropyl ether (20 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C
  5. customThe product thus obtained (7.2 g)
  6. dissolutionis dissolved
  7. filtrationis filtered hot
  8. temperaturethe filtrate is then cooled for 1 hour at a temperature of about 5° C
  9. filtrationThe resulting crystals are filtered off
  10. washwashed with ethanol (5 cc)
  11. dry with materialtwice with diisopropyl ether (14 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C

Sources & evidence

ORD record
ord-eba34a5eb9e94ff5a8fef4ac7761532d
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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