Picolyl chloride hydrochloride → 2-(2-Pyridiniomethyl)isothiouronium dichloride

HRID 1701895Notes

Reaction equation

HRID 1701895 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[NH2:10][C:11]([NH2:13])=[S:12]>C(O)C>[ClH:2].[ClH:1].[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][S:12][C:11](=[NH:10])[NH2:13]

Participants

4

Reactant 2

HCID 23392Picolyl chloride hydrochlorideHCID 2723790Thiourea

Product 1

HCID 130439522-(2-Pyridiniomethyl)isothiouronium dichlorideYield 94.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-chloromethylpyridine hydrochloride (30 g) in ethanol (100 cc), at 60° C., is added dropwise and in the course of 15 minutes to a suspension of thiourea (17.6 g) in boiling ethanol (100 cc). Boiling is maintained for 90 minutes and then, after cooling, the resulting crystals are filtered off, washed twice with ethanol (100 cc in total) and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C., in the presence of potassium hydroxide pellets. 2-(Pyrid-2-ylmethyl)isothiourea dihydrochloride (41.7 g), melting at 220° C., is thus obtained.

Workup

  1. temperatureBoiling is maintained for 90 minutes
  2. temperatureafter cooling
  3. filtrationthe resulting crystals are filtered off
  4. washwashed twice with ethanol (100 cc in total)
  5. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C., in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-c0309a1094244c5394fbaa5aef71c9a8
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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