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

HRID 1385999Notes

Reaction equation

HRID 1385999 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-pyridazinecarbothioamide

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 stiffed in DIPE (100 ml), filtered off and dried, yielding 3.lg (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. filtrationfiltered off
  6. customdried

Sources & evidence

ORD record
ord-bab109de64834d62a2577824483e6111
Source dataset
uspto-grants-2001_07
Patent number
US06265407B1

Reaction notes

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