Potassium borohydride → HCID 23458675, compound

HRID 1679942Notes

Reaction equation

HRID 1679942 reaction equation
[OH:1][C:2]1([CH2:14][S:15][CH3:16])[CH2:6][S:5][C:4](=[S:7])[N:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[BH4-].[K+]>CO.O.C1CCCCC1.C(OCC)(=O)C>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:3][C:4](=[S:7])[S:5][CH2:6][CH:2]([OH:1])[CH2:14][S:15][CH3:16]

Participants

7

Reactant 2

HCID 4192641Potassium borohydrideHCID 23458653HCID 23458653, compound

Product 1

HCID 23458675HCID 23458675, compoundYield 89.8%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure of Example 3 is followed, but a suspension of 4-hydroxy-4-methylthiomethyl-3-(pyrid-2-yl)-thiazolidine-2-thione (13.6 g) in methanol (160 cc) and a solution of potassium borohydride (2.7 g) in distilled water (40 cc) are used as the starting materials at a maximum of 30° C. The reaction is allowed to proceed for 150 minutes at between 20° and 30° C. The crude product (13.5 g) is dissolved in a mixture of cyclohexane (80 cc) and ethyl acetate (20 cc). The solution is chromatographed on silica (0.2-0.5 mm, 300 g) contained in a column of diameter 4 cm. Elution is carried out first with a mixture of cyclohexane (800 cc) and ethyl acetate (200 cc), this eluate being discarded, and then with a mixture of cyclohexane (1,600 cc) and ethyl acetate (450 cc), this eluate being collected and evaporated under reduced pressure (20 mm Hg) at 45° C. and then dried under reduced pressure (0.2 mm Hg) at 50° C. 2-Hydroxy-3 -methylthiopropyl pyrid-2-yldithiocarbamate (12.3 g) 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, 300 g)
  3. washElution
  4. additionis carried out first with a mixture of cyclohexane (800 cc) and ethyl acetate (200 cc)
  5. additionwith a mixture of cyclohexane (1,600 cc) and ethyl acetate (450 cc)
  6. customthis eluate being collected
  7. customevaporated under reduced pressure (20 mm Hg) at 45° C.
  8. customdried under reduced pressure (0.2 mm Hg) at 50° C

Sources & evidence

ORD record
ord-765794542d224220ac4f93c6f55a95b3
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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