Potassium borohydride → HCID 23458690, compound

HRID 1679950Notes

Reaction equation

HRID 1679950 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[S:21])[S:10][CH2:11][CH2:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:6][CH:7]=1.[BH4-].[K+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[S:21])[S:10][CH2:11][CH2:12][CH:13]([OH:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 4192641Potassium borohydrideHCID 23458660HCID 23458660, compound

Product 1

HCID 23458690HCID 23458690, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The procedure of Example 3 is followed, but a suspension of 3-oxo-3-phenylpropyl 5-chloropyrid-2-yldithiocarbamate (28.0 g) in methanol (840 cc) and a solution of potassium borohydride (9.0 g) in distilled water (120 cc) are used as the starting materials at a maximum of 30° C. The reaction is allowed to proceed for 20 hours at between 20° and 25° C. Unreacted starting material (5.5 g) is filtered off from the reaction mixture. The filtrate is evaporated to dryness. The residue (20.0 g) is dissolved in chloroform (200 cc). The solution is chromatographed on silica (0.063-0.2 mm, 400 g) contained in a column of diameter 5 cm. Elution is carried out with chloroform (2 liters), this eluate being discarded, and then with chloroform (4.5 liters). The eluate which is collected is evaporated to dryness under reduced pressure (20 mm Hg) at 45° C. The chromatographed product (14.4 g) is recrystallised from acetonitrile (40 cc). 3-Hydroxy-3-phenylpropyl 5-chloropyrid-2-yldithiocarbamate (9.8 g), which melts at 91° C., is obtained.

Workup

  1. customare used as the starting materials at a maximum of 30° C
  2. filtrationis filtered off from the reaction mixture
  3. customThe filtrate is evaporated to dryness
  4. dissolutionThe residue (20.0 g) is dissolved in chloroform (200 cc)
  5. customThe solution is chromatographed on silica (0.063-0.2 mm, 400 g)
  6. washElution
  7. customThe eluate which is collected
  8. customis evaporated to dryness under reduced pressure (20 mm Hg) at 45° C
  9. customThe chromatographed product (14.4 g) is recrystallised from acetonitrile (40 cc)

Sources & evidence

ORD record
ord-a0e582181f8a454da92876a841796500
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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