4-(Chloromethyl)pyridinium chloride → HCID 13043949, compound

HRID 1701887Notes

Reaction equation

HRID 1701887 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[NH2:10][C:11]([NH2:13])=[S:12]>C(O)C>[ClH:2].[ClH:1].[N:7]1[CH:8]=[CH:9][C:4]([CH2:3][S:12][C:11](=[NH:10])[NH2:13])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 2723790Thiourea

Product 1

HCID 13043949HCID 13043949, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
5 °C

Procedure

A suspension of 4-chloromethylpyridine hydrochloride (82 g) in gently boiling ethanol (260 cc) is added dropwise and in the course of 30 minutes to a suspension of thiourea (45.5 g) in boiling ethanol (260 cc). The reaction mixture is stirred for 1 hour 30 minutes at the boil and then cooled to 5° C. The resulting crystals are filtered off, washed twice with ethanol (60 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. 2-(Pyrid-4-yl-methyl)-isothiourea dihydrochloride (116 g), melting at 260° C., is thus obtained.

Workup

  1. filtrationThe resulting crystals are filtered off
  2. washwashed twice with ethanol (60 cc in total)
  3. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C

Sources & evidence

ORD record
ord-f592ffd2461b480db1d2bc222e33c46b
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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