Methane → N-methyl-2-(pyrid-2-yl)-tetrahydrothiopyran-2-carbothioamide

HRID 1701891Notes

Reaction equation

HRID 1701891 reaction equation
[CH3:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:15]([S:17]C)=S)[CH2:14][CH2:13][CH2:12][CH2:11][S:10]1.C>C(O)C>[CH3:1][NH:2][C:15]([C:9]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11][S:10]1)=[S:17]

Participants

5

Reactant 3

HCID 297MethaneHCID 6329MethylamineHCID 13043960Methyl 2-(pyrid-2-yl)-tetrahydrothiopyran-2-carbodithioate

Product 1

HCID 13139530N-methyl-2-(pyrid-2-yl)-tetrahydrothiopyran-2-carbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
20 °C

Procedure

A 33% (weight/volume) solution of methylamine in ethanol (7.5 cc) is added dropwise and in the course of 15 minutes to a solution of methyl 2-(pyrid-2-yl)-tetrahydrothiopyran-2-carbodithioate (9 g) in ethanol (60 cc), kept at a temperature of about 20° C. The solution is then stirred for 16 hours at a temperature of about 20° C. The resulting crystals are filtered off, washed twice with ethanol (20 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. A crystalline crude product (7.8 g) is thus obtained, which is redissolved in boiling ethanol (96 cc); decolourising charcoal (0.4 g) is added to the solution thus obtained, which is filtered hot, and the filtrate is then cooled for 30 minutes at 0° C. The resulting crystals are filtered off, washed twice with ethanol (20 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 45° C. N-Methyl-2-(pyrid-2-yl)-tetrahydrothiopyran-2-carbothioamide (6.3 g), melting at 153° C., is thus obtained.

Workup

  1. customkept at a temperature of about 20° C
  2. filtrationThe resulting crystals are filtered off
  3. washwashed twice with ethanol (20 cc in total)
  4. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C
  5. customA crystalline crude product (7.8 g) is thus obtained
  6. dissolutionwhich is redissolved
  7. customthus obtained
  8. filtrationwhich is filtered hot
  9. temperaturethe filtrate is then cooled for 30 minutes at 0° C
  10. filtrationThe resulting crystals are filtered off
  11. washwashed twice with ethanol (20 cc in total)
  12. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 45° C

Sources & evidence

ORD record
ord-0a8c3f18938e4f8db86b25368e529eef
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

Loading…