1-Heptanamine → HCID 13720644, compound

HRID 1680190Notes

Reaction equation

HRID 1680190 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]([NH2:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(O)C>[CH2:16]([NH:23][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][CH3:22]

Participants

4

Reactant 2

HCID 81271-HeptanamineHCID 13720640HCID 13720640, compound

Product 1

HCID 13720644HCID 13720644, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-(pyrid-2-yl)tetrahydrothiophene-2-carbodithioate (6.4 g) and n-heptylamine (2.9 g) in ethanol (75 cc) is heated under reflux for 2 hours 30 minutes. The reaction mixture is concentrated to dryness (20 mm Hg; 2.7 kPa) at 40° C. 6.8 g of a product prepared under the same conditions are added to the resulting residue (8.2 g) and the whole is chromatographed on neutral silica gel (150 g) contained in a column of diameter 3.5 cm. Elution is carried out with a cyclohexane-ethyl acetate mixture (98:2 by volume; 7300 cc), the following fractions of eluate being collected: fraction 1: 600 cc, fractions 2 to 8: 250 cc each and fractions 9 to 47: 100 cc each. Fractions 14 to 40 are combined and concentrated to dryness under reduced pressure (2 mm Hg; 0.27 kPa) at a temperature of 40° C. N-n-Heptyl-2-(pyrid-2-yl)tetrahydrothiophene-2-carbothioamide (8.3 g) is thus obtained in the form of a clear yellow liquid [Rf=0.40; chromatography on a thin layer of silica gel; solvent: cyclohexane-ethyl acetate (80:20 by volume)].

Workup

  1. temperatureunder reflux for 2 hours 30 minutes
  2. concentrationThe reaction mixture is concentrated to dryness (20 mm Hg; 2.7 kPa) at 40° C
  3. custom6.8 g of a product prepared under the same conditions
  4. customthe whole is chromatographed on neutral silica gel (150 g)
  5. washElution
  6. customthe following fractions of eluate being collected
  7. concentrationconcentrated to dryness under reduced pressure (2 mm Hg; 0.27 kPa) at a temperature of 40° C

Sources & evidence

ORD record
ord-11581a6ba817469887fd91c210d45add
Source dataset
uspto-grants-1981_06
Patent number
US04272534

Reaction notes

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