Sodium hydride → 6-[[4-[3-(Trifluoromethyl)-phenoxy]butyl]thio]-3-pyridazinecarbothioamide

HRID 394488Notes

Reaction equation

HRID 394488 reaction equation
[SH:1][C:2]1[N:7]=[N:6][C:5]([C:8](=[S:10])[NH2:9])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1>CN(C=O)C>[F:26][C:25]([F:27])([F:28])[C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][CH2:17][CH2:16][CH2:15][CH2:14][S:1][C:2]1[N:7]=[N:6][C:5]([C:8](=[S:10])[NH2:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129286411-(4-Chlorobutoxy)-3-(trifluoromethyl)-benzeneHCID 178514135HCID 178514135, compound

Product 1

HCID 181766426-[[4-[3-(Trifluoromethyl)-phenoxy]butyl]thio]-3-pyridazinecarbothioamideYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of intermediate 11 (0.017 mol) in DMF (80 ml) was stirred at room temperature. Sodium hydride (50%, 0.02 mol) was added portionwise. The mixture was stirred for 30 minutes. A mixture of 1-(4-chlorobutoxy)-3-(trifluoromethyl)-benzene (0.02 mol) in DMF (20 ml) was added dropwise. The mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was stirred in DIPE (100 ml), filtered off and dried, yielding 3.1 g (47%) of 6-[[4-[3-(trifluoromethyl)-phenoxy]butyl]thio]-3-pyridazinecarbothioamide (intermediate 12).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. additionwas added dropwise
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThe solvent was evaporated
  5. stirringThe residue was stirred in DIPE (100 ml)
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-8da87fa6bb7c48b6a499ea97f4c6e60d
Source dataset
uspto-grants-2003_08
Patent number
US06602873B2

Reaction notes

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