Dimethylamine → HCID 13720654, compound

HRID 1680193Notes

Reaction equation

HRID 1680193 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([C:12]([S:14]C)=S)[CH2:11][CH2:10][CH2:9][S:8]1.[CH3:16][NH:17][CH3:18]>>[CH3:16][N:17]([CH3:18])[C:12]([C:7]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:11][CH2:10][CH2:9][S:8]1)=[S:14]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 13720640HCID 13720640, compound

Product 1

HCID 13720654HCID 13720654, compound

Conditions

Temperature
20 °C

Procedure

A solution of methyl 2-(pyrid-2-yl)tetrahydrothiophene-2-carbodithioate (20 g) in dimethylamine (100 cc) is heated gradually for 3 hours 40 minutes, in an autoclave, up to a temperature of about 125° C. After cooling to a temperature of about 20° C., the autoclave is emptied and rinsed with methylene chloride (200 cc), the latter being added to the reaction mixture. The solution is concentrated to dryness (20 mm Hg; 2.7 kPa) at 40° C. The resulting residue (20.7 g) is dissolved in boiling ethanol (50 cc) and the solution, to which decolourising charcoal (0.5 g) is added, is filtered hot and then kept, after cooling, for 1 hour at a temperature of about 0° C. The crystals which have appeared 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. The resulting product (14.1 g) is dissolved in boiling ethanol (45 cc) and the solution, to which decolourising charcoal (0.5 g) is added, is filtered hot and then kept, after cooling, for 1 hour at a temperature of 0° C. The crystals which have appeared 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,N-Dimethyl-2-(pyrid-2-yl)-tetrahydrothiophene-2-carbothioamide (11.8 g), melting at 100° C., is thus obtained.

Workup

  1. washrinsed with methylene chloride (200 cc)
  2. additionthe latter being added to the reaction mixture
  3. concentrationThe solution is concentrated to dryness (20 mm Hg; 2.7 kPa) at 40° C
  4. dissolutionThe resulting residue (20.7 g) is dissolved
  5. additionis added
  6. filtrationis filtered hot
  7. temperatureafter cooling, for 1 hour at a temperature of about 0° C
  8. filtrationThe crystals which have appeared are filtered off
  9. washwashed twice with ethanol (20 cc in total)
  10. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C
  11. dissolutionThe resulting product (14.1 g) is dissolved
  12. additionis added
  13. filtrationis filtered hot
  14. temperatureafter cooling, for 1 hour at a temperature of 0° C
  15. filtrationThe crystals which have appeared are filtered off
  16. washwashed twice with ethanol (20 cc in total)
  17. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 45° C

Sources & evidence

ORD record
ord-885fee2c409648ac9b8ac40754b2c9d3
Source dataset
uspto-grants-1981_06
Patent number
US04272534

Reaction notes

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