Triethylamine → 4-Methyl-5-trifluoromethyl-3-(1,2-dichloro-2-cyanovinyl thio)-1,2,4-triazole

HRID 1632728Notes

Reaction equation

HRID 1632728 reaction equation
[SH:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]([F:11])([F:10])[F:9])=[N:4][N:3]=1.[Cl:12][C:13](Cl)=[C:14]([Cl:17])[C:15]#[N:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:7][N:6]1[C:5]([C:8]([F:9])([F:11])[F:10])=[N:4][N:3]=[C:2]1[S:1][C:13]([Cl:12])=[C:14]([Cl:17])[C:15]#[N:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 853312,3,3-Trichloro-2-propenenitrileHCID 178481704HCID 178481704, compound2×

Product 1

HCID 545611114-Methyl-5-trifluoromethyl-3-(1,2-dichloro-2-cyanovinyl thio)-1,2,4-triazoleYield 25.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 3.5 g (0.0192 mole) 3-mercapto-4-methyl-5-trifluoromethyl-1,2,4-triazole (the product of Example 6) and 3.0 g (0.0192 mole) trichloro-acrylonitrile in methylene chloride, 1.94 g (0.0192 mole) triethylamine in methylene chloride were added dropwise. The reaction mixture was stirred at room temperature for several days. The reaction mixture was washed with water and then dried over magnesium sulfate. The organic phase was passed through a short silica gel (SiO2) column and stripped to give a thick oil which soon crystallized. The material was recrystallized from methylene chloride/hexane to give 1.5 g of the above-identified product as a light yellow solid, melting point 90°-94° C.

Workup

  1. additionwere added dropwise
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customto give a thick oil which
  5. customsoon crystallized
  6. customThe material was recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-4ccf332290194fc8a958458b6d2ed95b
Source dataset
uspto-grants-1984_10
Patent number
US04477459

Reaction notes

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