Hydrochloric Acid → HCID 23458682, compound

HRID 1679946Notes

Reaction equation

HRID 1679946 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[S:20])[S:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[N:6][CH:7]=1.[BH4-].[K+].Cl>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[S:20])[S:10][CH2:11][CH:12]([OH:13])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3052879Carbamodithioic acid, (5-chloro-2-pyridinyl)-, 2-oxo-2-phenylethyl esterHCID 4192641Potassium borohydride

Product 1

HCID 23458682HCID 23458682, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The procedure of Example 8 is followed, but a suspension of phenacyl 5-chloropyrid-2-yldithiocarbamate (23.1 g) in acetonitrile (240 cc) and a solution of potassium borohydride (3.9 g) in distilled water (60 cc) are used as the starting materials at between 20° and 28° C. The reaction is allowed to proceed for 45 minutes at 25° C. After adding a 3 N aqueous solution of hydrochloric acid (23.8 cc), filtering off the crystals, washing them with ice-cooled acetonitrile (15 cc) and then three times with distilled water (180 cc in total) and drying them under reduced pressure (0.2 mm Hg) at 40° C., 2-hydroxy-2-phenylethyl 5-chloropyrid-2-yldithiocarbamate (13.6 g), which melts at 116° C., is obtained.

Workup

  1. customare used as the starting materials at between 20° and 28° C
  2. filtrationfiltering off the crystals
  3. washwashing them with ice-
  4. temperaturecooled acetonitrile (15 cc)
  5. dry with materialthree times with distilled water (180 cc in total) and drying them under reduced pressure (0.2 mm Hg) at 40° C.

Sources & evidence

ORD record
ord-5c02f9600a304fe0b456b97451af2e44
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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