1-Bromo-3-chloropropane → HCID 86613316, compound

HRID 1442654Notes

Reaction equation

HRID 1442654 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[N:18]1[C:22]([NH:23][CH3:24])=[C:21]([S:25][C:26]([F:29])([F:28])[F:27])[C:20]([C:30]#[N:31])=[N:19]1.[H-].[Na+].CCCCCCC.C(OCC)(=O)C>O1CCCC1.O>[Cl:5][CH2:4][CH2:3][CH2:2][N:23]([C:22]1[N:18]([C:8]2[C:9]([Cl:17])=[CH:10][C:11]([C:13]([F:14])([F:15])[F:16])=[CH:12][C:7]=2[Cl:6])[N:19]=[C:20]([C:30]#[N:31])[C:21]=1[S:25][C:26]([F:29])([F:28])[F:27])[CH3:24]

Participants

7

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 21899848Ethylacetate heptaneHCID 22618614HCID 22618614, compound

Product 1

HCID 86613316HCID 86613316, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Bromo-3-chloropropane (1.62 g, 1.6 mmol) was added to a mixture of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylthiopyrazole (3.0 g, 6.9 mmol) and sodium hydride (0.35 g, 8.9 mmol) in tetrahydrofuran (45 ml) under a nitrogen atmosphere, and the mixture heated under reflux for 6 hours. After extractive workup (heptane-ethyl acetate, water) and chromatography the title product was obtained as a solid (1.83 g); 1H-NMR: 1.81 (2H), 2.88 (3H), 3.21 (2H), 3.37 (2H), 7.80 (2H); 19F-NMR: −44.8; −64.2 ppm.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 6 hours

Sources & evidence

ORD record
ord-da8f14ea6674426da39b6c81d92d2964
Source dataset
uspto-grants-2010_02
Patent number
US07659288B2

Reaction notes

Loading…