Thionyl Chloride → HCID 22247817, compound

HRID 889853Notes

Reaction equation

HRID 889853 reaction equation
O[CH2:2][CH2:3][N:4]1[CH:8]=[N:7][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:5]1.S(Cl)([Cl:17])=O>>[Cl:17][CH2:2][CH2:3][N:4]1[CH:8]=[N:7][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:5]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22247836HCID 22247836, compound

Product 1

HCID 22247817HCID 22247817, compound

Conditions

Temperature
70 °C

Procedure

122 g (6.4 mmol) 1-(2-hydroxyethyl)-3-(3-pyridinyl)-1H-1,2,4-triazole were suspended in 15 ml thionyl chloride and heated at 70° C. for 45 minutes. Excess thionyl chloride was removed in vacuo and the residue was dissolved in water (100 ml). The aqueous solution was basified with NaHCO3 solution (10%) and the resulting slurry was stirred for 15 minutes. The product was isolated by filtration, washed with water and dried to give the desired product as a brownish solid. MS (EI): 208.1 (M+). 1H-NMR (DMSO-d6): 3.97 (t, 2H), 4.54 (t, 2H), 7.38 (m, 1H), 8.21 (s, 1H), 8.36 (m, 1H), 8.65 (m, 1H), 9.34 (d, 1H).

Workup

  1. customExcess thionyl chloride was removed in vacuo
  2. dissolutionthe residue was dissolved in water (100 ml)
  3. customThe product was isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c56ecc9aca6c4fd2a7a4dea4725cc06a
Source dataset
uspto-grants-2006_02
Patent number
US06995143B2

Reaction notes

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