1-Penten-3-one → HCID 23458239, compound

HRID 1679874Notes

Reaction equation

HRID 1679874 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[S:10])[S-:9].C([NH+](CC)CC)C.[CH2:18]=[CH:19][C:20](=[O:23])[CH2:21][CH3:22]>C(#N)C.C(Cl)(Cl)Cl.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[S:9])[S:10][CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH3:22]

Participants

6

Reactant 2

HCID 153941-Penten-3-oneHCID 15899924HCID 15899924, compound

Product 1

HCID 23458239HCID 23458239, compoundYield 31.6%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure of Example 2 is followed but triethylammonium pyrid-2-yldithiocarbamate (54.0 g) and pent-1-en-3-one (17.0 g) in anhydrous acetonitrile (400 cc) are used as the starting materials at a maximum temperature of 5° C. The reaction is allowed to proceed for 3 hours at between 5° and 20° C. The crude product (45.0 g) is dissolved in a mixture of chloroform (200 cc) and ethyl acetate (50 cc). The solution is chromatographed on a column of diameter 6 cm, containing silica (0.063-0.2 mm; 600 g). Elution is carried out with a mixture of chloroform (400 cc) and ethyl acetate (100 cc), this eluate being discarded, and then with a mixture of chloroform (2,800 cc) and ethyl acetate (700 cc), this eluate being collected and evaporated to dryness under reduced pressure (20 mmHg) at 45° C. The product obtained (30.0 g) is purified by recrystallisation from a mixture of acetonitrile (30 cc) and diisopropyl ether (60 cc). 3-Oxopentyl pyrid-2-yldithiocarbamate (16.0 g) (structure determined by IR spectroscopy in petroleum jelly), which melts at 80° C., is obtained.

Workup

  1. customare used as the starting materials at a maximum temperature of 5° C
  2. customThe solution is chromatographed on a column of diameter 6 cm
  3. additioncontaining silica (0.063-0.2 mm; 600 g)
  4. washElution
  5. additionis carried out with a mixture of chloroform (400 cc) and ethyl acetate (100 cc)
  6. additionwith a mixture of chloroform (2,800 cc) and ethyl acetate (700 cc)
  7. customthis eluate being collected
  8. customevaporated to dryness under reduced pressure (20 mmHg) at 45° C
  9. customThe product obtained (30.0 g)
  10. customis purified by recrystallisation from a mixture of acetonitrile (30 cc) and diisopropyl ether (60 cc)

Sources & evidence

ORD record
ord-c0755720b613405db037fe2142d4e948
Source dataset
uspto-grants-1981_06
Patent number
US04271156

Reaction notes

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