Dodecylamine → HCID 13720645, compound

HRID 1680191Notes

Reaction equation

HRID 1680191 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.[CH2:16]([NH2:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>>[CH2:16]([NH:28][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])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

3

Reactant 2

HCID 13583DodecylamineHCID 13720640HCID 13720640, compound

Product 1

HCID 13720645HCID 13720645, compoundYield 66.3%

Conditions

Temperature
0 °C

Procedure

A solution of methyl 2-(pyrid-2-yl)tetrahydrothiophene-2-carbodithioate (10 g) in n-dodecylamine (15 g) is heated for 50 minutes at 110° C. The reaction mixture is chromatographed on silica gel (200 g) contained in a column of diameter 3.7 cm. Elution is carried out with a cyclohexane-ethyl acetate mixture (90:10 by volume; 1800 cc), one 300 cc fraction and three 500 cc fractions being collected. Fractions 2 to 4 are combined and concentrated to dryness (20 mm Hg; 2.7 kPa) at 40° C.; the residue (14.2 g) is dissolved in ethanol (75 cc). The solution, to which decolourising charcoal (0.3 g) is added, is filtered hot and then kept, after cooling, for 30 minutes at a temperature of about 0° C. The crystals which have appeared are filtered off, washed twice with ethanol (40 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. The resulting product (11.5 g) is dissolved in boiling ethanol (75 cc) and the solution, to which decolourising charcoal (0.3 g) is added, is filtered hot and then kept, after cooling, for 30 minutes at a temperature of about 0° C. The crystals which have appeared are filtered off, washed twice with ethanol (50 cc in total) and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 35° C. N-n-Dodecyl-2-(pyrid-2-yl)tetrahydrothiophene-2-carbothioamide (10.2 g), melting at 60° C., is thus obtained.

Workup

  1. customThe reaction mixture is chromatographed on silica gel (200 g)
  2. washElution
  3. custombeing collected
  4. concentrationconcentrated to dryness (20 mm Hg; 2.7 kPa) at 40° C.
  5. dissolutionthe residue (14.2 g) is dissolved in ethanol (75 cc)
  6. additionis added
  7. filtrationis filtered hot
  8. filtrationThe crystals which have appeared are filtered off
  9. washwashed twice with ethanol (40 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 (11.5 g) is dissolved
  12. additionis added
  13. filtrationis filtered hot
  14. temperatureafter cooling, for 30 minutes at a temperature of about 0° C
  15. filtrationThe crystals which have appeared are filtered off
  16. washwashed twice with ethanol (50 cc in total)
  17. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 35° C

Sources & evidence

ORD record
ord-1323081aa0d04f19bad48a2f7156014e
Source dataset
uspto-grants-1981_06
Patent number
US04272534

Reaction notes

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