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

HRID 1632726Notes

Reaction equation

HRID 1632726 reaction equation
[CH2:1]([N:4]1[C:8]([C:9]([F:12])([F:11])[F:10])=[N:7][N:6]=[C:5]1[SH:13])[CH:2]=[CH2:3].[Cl:14][C:15](Cl)=[C:16]([Cl:19])[C:17]#[N:18].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:4]1[C:8]([C:9]([F:11])([F:12])[F:10])=[N:7][N:6]=[C:5]1[S:13][C:15]([Cl:14])=[C:16]([Cl:19])[C:17]#[N:18])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 853312,3,3-Trichloro-2-propenenitrile2×HCID 178456616HCID 178456616, compound2×

Product 1

HCID 540523024-Allyl-5-trifluoromethyl-3-(1,2-dichloro-2-cyanovinyl thio)-1,2,4-triazoleYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.0 g (0.019 mole) 4-allyl-5-trifluoromethyl-3-mercapto-1,2,4-triazole (the product of Example 2), 3.0 g (0.019 mole) trichloroacrylonitrile (the product of Example 3A), and 2.65 ml (0.019 mole) triethylamine in 100 ml methylene chloride was stirred at room temperature for several days. The reaction mixture washed with water, dried over magnesium sulfate, and stripped to give a yellow oil. Further purification by chromatography gave 3.6 g of the product as an oil which later crystallized, melting point 45°-48° C.

Workup

  1. washThe reaction mixture washed with water
  2. dry with materialdried over magnesium sulfate
  3. customto give a yellow oil
  4. customFurther purification by chromatography

Sources & evidence

ORD record
ord-faa2411a48474ec2a801c9851a766cbc
Source dataset
uspto-grants-1984_10
Patent number
US04477459

Reaction notes

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