3-(Chloromethyl)pyridine hydrochloride → HCID 13043947, compound

HRID 1701912Notes

Reaction equation

HRID 1701912 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[NH2:10][C:11]([NH2:13])=[S:12]>C(O)C>[ClH:2].[ClH:1].[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][S:12][C:11](=[NH:10])[NH2:13])[CH:5]=1

Participants

4

Reactant 2

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 2723790Thiourea

Product 1

HCID 13043947HCID 13043947, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
26 °C

Procedure

A solution of 3-chloromethylpyridine hydrochloride (164 g) in ethanol (510 cc), at 50° C., is added dropwise and in the course of 20 minutes to a solution of thiourea (91 g) in boiling ethanol (510 cc). The reaction mixture is stirred for 3 hours 50 minutes at the boil and then cooled to 26° C. The resulting crystals are filtered off, washed twice with ethanol (400 cc in total) and dried under reduced pressure (25 mm Hg; 2.7 kPa) at a temperature of about 20° C. 2-(Pyrid-3-ylmethyl)-isothiourea dihydrochloride (173 g), melting at 212° C., is thus obtained.

Workup

  1. filtrationThe resulting crystals are filtered off
  2. washwashed twice with ethanol (400 cc in total)
  3. customdried under reduced pressure (25 mm Hg; 2.7 kPa) at a temperature of about 20° C

Sources & evidence

ORD record
ord-3b23eaa2915e40edaf893b7ba1f95081
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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