1,4-Dibromobutane → HCID 18402923, compound

HRID 2270902Notes

Reaction equation

HRID 2270902 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5]Br.[Cl:7][C:8]1[C:13]([O:14][C:15]2[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:12][C:11]([N:25]=[C:26]2[S:30][C:29](=[O:31])[NH:28][NH:27]2)=[C:10]([F:32])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:7][C:8]1[C:13]([O:14][C:15]2[C:20]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:12][C:11]([N:25]=[C:26]2[N:27]3[N:28]([CH2:2][CH2:3][CH2:4][CH2:5]3)[C:29](=[O:31])[S:30]2)=[C:10]([F:32])[CH:9]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 178518851HCID 178518851, compound

Product 1

HCID 18402923HCID 18402923, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,4-Dibromobutane (0.64 g) was mixed with 5-[4-chloro-2-fluoro-5-(3-trifluoromethyl-2-pyridyloxy)phenylimino]-1,3,4-thiadiazolidin-2-one (1.0 g) in acetone (25 ml) and potassium carbonate (0.85 g) added. The mixture was heated at reflux for 2 hours and the solvent evaporated. The residue was processed and the resulting oil chromatographed (silica gel, hexane:ethyl acetate, 4:1) to give the product (0.65 g, 57%).

Workup

  1. additionadded
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 hours
  4. customthe solvent evaporated
  5. customthe resulting oil chromatographed (silica gel, hexane:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-a02cf608b09848f8b54c900272764e5d
Source dataset
uspto-grants-2001_12
Patent number
US06333296B1

Reaction notes

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