Potassium borohydride → HCID 23458670, compound

HRID 1679953Notes

Reaction equation

HRID 1679953 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:12](=[O:13])[CH2:11][CH2:10][S:9][C:8]1=[S:14].[BH4-].[K+]>CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[S:14])[S:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 2

HCID 4192641Potassium borohydrideHCID 23458677HCID 23458677, compound

Product 1

HCID 23458670HCID 23458670, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The procedure of Example 24 is followed, but a suspension of 3-(pyrid-2-yl)-2-thioxo-perhydro-1,3-thiazin-4-one (22.4 g) in methanol (300 cc) and a solution of potassium borohydride (10.8 g) in distilled water (75 cc) are used as the starting materials at a maximum of 40° C. The reaction is allowed to proceed for 1 hour at between 25° and 40° C. The reaction mixture is evaporated to dryness and the residue (21.5 g) is dissolved in a mixture of ethyl acetate (70 cc) and cyclohexane (30 cc). The solution is chromatographed on silica (0.2-0.5 mm) (300 g) distributed in a column of diameter 4.5 cm. Elution is carried out with a mixture of ethyl acetate (520 cc) and cyclohexane (180 cc), this eluate being discarded, and then with a mixture of ethyl acetate (1,660 cc) and cyclohexane (540 cc). The eluate which is collected is evaporated to dryness under reduced pressure (20 mm Hg) at 45° C. 3-Hydroxypropyl pyrid-2-yldithiocarbamate (12.2 g), which melts at 93° C., is obtained.

Workup

  1. customare used as the starting materials at a maximum of 40° C
  2. customThe reaction mixture is evaporated to dryness
  3. dissolutionthe residue (21.5 g) is dissolved in a mixture of ethyl acetate (70 cc) and cyclohexane (30 cc)
  4. customThe solution is chromatographed on silica (0.2-0.5 mm) (300 g)
  5. washElution
  6. additionis carried out with a mixture of ethyl acetate (520 cc) and cyclohexane (180 cc)
  7. additionwith a mixture of ethyl acetate (1,660 cc) and cyclohexane (540 cc)
  8. customThe eluate which is collected
  9. customis evaporated to dryness under reduced pressure (20 mm Hg) at 45° C

Sources & evidence

ORD record
ord-31d88b5dac7447bdb0b8161cf4f1b07d
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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