Thionyl Chloride → 5-Chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine

HRID 445918Notes

Reaction equation

HRID 445918 reaction equation
[NH2:1][C:2]1[C:3](=O)[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:9]=2[CH3:17])[NH:6][N:7]=1.S(Cl)([Cl:21])=O>>[Cl:21][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:9]=2[CH3:17])[N:6]=[N:7][C:2]=1[NH2:1]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178422338HCID 178422338, compound

Product 1

HCID 582795485-Chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amineYield 102.7%

Procedure

A suspension of 6-amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5(2H)-one (0.95 g, 3.38 mmol) in thionyl chloride (180 mL, 2466 mmol) was heated at reflux for 4 hr, after which period the mixture became a clear solution. The volatiles were removed under vacuum. The residue was dissolved in ice-cold ethyl acetate (250 mL), washed with water (2×60 mL), saturated NaHCO3 solution (60 mL), and brine (60 mL). The organic solution was dried over anhydrous MgSO4 and concentrated under vacuum to dryness to provide the desired product, 5-chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine (0.97 g, 3.47 mmol, 77% yield over two steps), as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hr
  3. customThe volatiles were removed under vacuum
  4. dissolutionThe residue was dissolved in ice-cold ethyl acetate (250 mL)
  5. washwashed with water (2×60 mL), saturated NaHCO3 solution (60 mL), and brine (60 mL)
  6. dry with materialThe organic solution was dried over anhydrous MgSO4
  7. concentrationconcentrated under vacuum to dryness

Sources & evidence

ORD record
ord-c1459952adc742bc9af2668eb88cd0d5
Source dataset
uspto-grants-2013_07
Patent number
US08476430B2

Reaction notes

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