Hydrochloric Acid → HCID 23458663, compound

HRID 1679940Notes

Reaction equation

HRID 1679940 reaction equation
[BH4-].[K+].[OH:3][C:4]1([CH2:16][OH:17])[CH2:8][S:7][C:6](=[S:9])[N:5]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Cl>O.C(#N)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:5][C:6](=[S:9])[S:7][CH2:8][CH:4]([OH:3])[CH2:16][OH:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4192641Potassium borohydrideHCID 23458683HCID 23458683, compound

Product 1

HCID 23458663HCID 23458663, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
2 °C

Procedure

A solution of potassium borohydride (5.4 g) in distilled water (35 cc) is added, at a maximum of 20° C., to a suspension of 4-hydroxy-4-hydroxymethyl-3-(pyrid-2-yl)-thiazolidine-2-thione (23.8 g) in anhydrous acetonitrile (240 cc). The reaction is allowed to proceed for 30 minutes at 20° C. An 8.5 N aqueous solution of hydrochloric acid (12 cc) is added at a maximum of 20° C. The acetonitrile is evaporated off under reduced pressure (20 mm Hg) at 45° C. The aqueous phase is extracted 3 times with chloroform (500 cc in total). The organic solution is washed with distilled water (100 cc), dried over sodium sulphate and evaporated. The resulting product (21.2 g) is purified by crystallisation from a mixture of methylene chloride (100 cc) and isopropyl ether (50 cc). After drying in the atmosphere for 16 hours, yellow crystals (13 g), which melt at 96° C., are obtained and these are purified again by recrystallisation from a boiling mixture of acetonitrile (75 cc) and isopropyl ether (20 cc). After filtering the boiling solution and then cooling for 2 hours at 2° C., the crystals which have appeared are filtered off, washed with an ice-cooled mixture (25 cc in total) of acetonitrile (20 cc) and isopropyl ether (5 cc) and dried under reduced pressure (0.1 mm Hg) at 45° C. 2,3-Dihydroxy-propyl pyrid-2-yldithiocarbamate (10.2 g), which melts at 98° C., is thus obtained.

Workup

  1. customThe acetonitrile is evaporated off under reduced pressure (20 mm Hg) at 45° C
  2. extractionThe aqueous phase is extracted 3 times with chloroform (500 cc in total)
  3. washThe organic solution is washed with distilled water (100 cc)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe resulting product (21.2 g) is purified by crystallisation from a mixture of methylene chloride (100 cc) and isopropyl ether (50 cc)
  7. customAfter drying in the atmosphere for 16 hours
  8. custommelt at 96° C.
  9. customare obtained
  10. customthese are purified again by recrystallisation from a boiling mixture of acetonitrile (75 cc) and isopropyl ether (20 cc)
  11. filtrationAfter filtering the boiling solution
  12. filtrationthe crystals which have appeared are filtered off
  13. washwashed with an ice-
  14. temperaturecooled mixture (25 cc in total) of acetonitrile (20 cc) and isopropyl ether (5 cc)
  15. customdried under reduced pressure (0.1 mm Hg) at 45° C

Sources & evidence

ORD record
ord-cb8687b60d7e440f89dc379b035db4d7
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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