Potassium borohydride → HCID 23458676, compound

HRID 1679947Notes

Reaction equation

HRID 1679947 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[S:16])[S:10][CH2:11][CH2:12][C:13](=[O:15])[CH3:14])=[N:6][CH:7]=1.[BH4-].[K+]>CO.O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[S:16])[S:10][CH2:11][CH2:12][CH:13]([OH:15])[CH3:14])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 4192641Potassium borohydrideHCID 234582413-Oxobutyl 5-chloropyrid-2-yldithiocarbamate

Product 1

HCID 23458676HCID 23458676, compoundYield 62.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The procedure of Example 3 is followed, but a suspension of 3-oxobutyl 5-chloropyrid-2-yldithiocarbamate (17.5 g) in methanol (220 cc) and a solution of potassium borohydride (3.44 g) in distilled water (55 cc) are used as the starting materials at a maximum of 30° C. The reaction is allowed to proceed for 1 hour at between 20° and 30° C. The resulting product (14.2 g; m.p.=115° C.) is dissolved in chloroform (500 cc). The solution is chromatographed on silica (0.2-0.5 mm) (140 g) contained in a column of diameter 3.4 cm. Elution is carried out with chloroform (1,500 cc), this eluate being discarded, and then with chloroform (4 liters). The eluate which is collected is evaporated to dryness under reduced pressure (20 mm Hg) at 45° C. The chromatographed product (11.4 g) is recrystallised from acetonitrile (85 cc). 3-Hydroxybutyl 5-chloropyrid-2-yldithiocarbamate (11.0 g), which melts at 122° C., is obtained.

Workup

  1. customare used as the starting materials at a maximum of 30° C
  2. customThe solution is chromatographed on silica (0.2-0.5 mm) (140 g)
  3. washElution
  4. customThe eluate which is collected
  5. customis evaporated to dryness under reduced pressure (20 mm Hg) at 45° C
  6. customThe chromatographed product (11.4 g) is recrystallised from acetonitrile (85 cc)

Sources & evidence

ORD record
ord-564aa2bdbc084dd891affd16bc731163
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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