Bromine → HCID 23119266, compound

HRID 1819500Notes

Reaction equation

HRID 1819500 reaction equation
[CH3:1][O:2][CH:3]([CH2:17][CH2:18][CH3:19])[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=O.BrBr.[NH2:22][C:23]([NH2:25])=[S:24].C(=O)([O-])O.[Na+]>C(O)C.CO.C(Cl)(Cl)Cl>[CH3:1][O:2][CH:3]([CH2:17][CH2:18][CH3:19])[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10]1[S:24][C:23]([NH2:25])=[N:22][C:11]=12

Participants

7

Reactant 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 23119404HCID 23119404, compound

Product 1

HCID 23119266HCID 23119266, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a 10% methanol-chloroform (60 mL) solution of 5-(3-methyloxyhexyl)tetralone (6) (9.0 g) was added bromine (5.5 g), and the reaction mixture was stirred for 1 h. After the solvent was evaoprated, the residue was dissolved in ethanol (60 mL), and to the residue was added thiourea (2.65 g). After the mixture was heated at reflux for 7 h, the reaction solvent was evported. To the residue was added a saturated sodium hydrogencarbonate aqueous solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1) to obtain the compoumd (7) 4.6 g.

Workup

  1. temperatureAfter the mixture was heated
  2. temperatureat reflux for 7 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-120f04d6ebd4443fbe2644a0d30ea18b
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

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