3-(Chloromethyl)pyridine hydrochloride → HCID 20505177, compound

HRID 1701883Notes

Reaction equation

HRID 1701883 reaction equation
Cl.[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].[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 20505177HCID 20505177, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
30 °C

Procedure

A solution of 3-chloromethylpyridine hydrochloride (100 g) in ethanol (310 cc), at 60° C. is added dropwise and in the course of 15 minutes to a suspension of thiourea (55 g) in boiling ethanol (310 cc). The reaction mixture is stirred for 1 hour 45 minutes at the boil and then cooled to 30° C. After decantation, the supernatant solution is discarded. Ethanol (400 cc) is added to the remaining gummy solid and the mixture is stirred for 63 hours at a temperature of about 20° 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-3-yl-methyl)isothiourea monohydrochloride (100 g), melting at 220° C. is thus obtained.

Workup

  1. stirringthe mixture is stirred for 63 hours at a temperature of about 20° C
  2. filtrationThe resulting crystals are filtered off
  3. washwashed twice with ethanol (60 cc in total)
  4. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C

Sources & evidence

ORD record
ord-a438054440a64a638b0790be0e732f5b
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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