Hydrochloric Acid → HCID 23458689, compound

HRID 1679939Notes

Reaction equation

HRID 1679939 reaction equation
[BH4-].[K+].[OH:3][C:4]1([CH3:16])[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.CO>[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])[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4192641Potassium borohydrideHCID 23458658HCID 23458658, compound

Product 1

HCID 23458689HCID 23458689, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium borohydride (5.4 g) in distilled water (80 cc) is added, at a maximum of 35° C., to a solution of 4-hydroxy-4-methyl-3-(pyrid-2-yl)-thiazolidine-2-thione (22.6 g) in methanol (320 cc). The reaction is allowed to proceed for 30 minutes at 25°-35° C. A 3 N aqueous solution of hydrochloric acid (33.2 cc) is added. The methanol is evaporated off under reduced pressure (20 mm Hg) at 45° C. The aqueous phase is extracted with ethyl ether (800 cc). The ether solution is washed twice with distilled water (300 cc in total), treated with decolourising charcoal (1 g), dried over sodium sulphate and evaporated. The resulting product (23.0 g) is purified by recrystallisation from a mixture of ethyl ether (100 cc) and isopropyl ether (100 cc). 2-Hydroxypropyl pyrid-2-yldithiocarbamate (11.1 g), which melts at 78° C., is obtained.

Workup

  1. customThe methanol is evaporated off under reduced pressure (20 mm Hg) at 45° C
  2. extractionThe aqueous phase is extracted with ethyl ether (800 cc)
  3. washThe ether solution is washed twice with distilled water (300 cc in total)
  4. additiontreated with decolourising charcoal (1 g)
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe resulting product (23.0 g) is purified by recrystallisation from a mixture of ethyl ether (100 cc) and isopropyl ether (100 cc)

Sources & evidence

ORD record
ord-446bc0e14ac848bd9073b131e3b79f2c
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

Loading…