Sodium Carbonate → 3,6-Dichloro-5-{[3-fluoro-5-(trifluoromethyl)phenyl]sulfanyl}-1,2,4-triazine

HRID 1472106Notes

Reaction equation

HRID 1472106 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[C:6](Cl)[N:7]=1.[F:10][C:11]1[CH:12]=[C:13]([SH:21])[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[C:6]([S:21][C:13]2[CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=[C:11]([F:10])[CH:12]=2)[N:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 122624033,5,6-Trichloro-1,2,4-triazineHCID 670547273-Fluoro-5-(trifluoromethyl)thiophenol

Product 1

HCID 866688233,6-Dichloro-5-{[3-fluoro-5-(trifluoromethyl)phenyl]sulfanyl}-1,2,4-triazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5,6-trichloro-1,2,4-triazine (3 mmol) in dry THF (30 mL) at −78° C. under nitrogen atmosphere is added 3-fluoro-5-(trifluoromethyl)benzenethiol (3 mmol) and sodium carbonate (3 mmol). The reaction is allowed to reach room temperature and is stirred at room temperature until formation of the desired compound. The solvent is evaporated. The residue is suspended in water and extracted with CH2Cl2. The dichloromethane solution is dried over MgSO4 and evaporated. The residue is chromatographed on a silica gel column.

Workup

  1. customto reach room temperature

Sources & evidence

ORD record
ord-e599684a16034b8b98a7108bd3de8c07
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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