Iodine → HCID 89740081, compound

HRID 1521797Notes

Reaction equation

HRID 1521797 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.[NH2:13][C:14]([NH2:16])=[S:15].II>C(O)C.O.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1[N:13]=[C:14]([NH2:16])[S:15][C:7]=1[CH2:6][CH2:5]2

Participants

7

Reactant 3

HCID 807IodineHCID 2723790ThioureaHCID 101050696-Bromo-1-tetralone

Product 1

HCID 89740081HCID 89740081, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

6-bromo-3,4-dihydronaphthalen-1(2H)-one (3.5 g, 15.55 mmol), thiourea (3.55 g, 46.6 mmol) and iodine (4.34 g, 17.10 mmol) were dissolved in 20 ml of ethanol and the solution was heated at 100° C. for 4 hr. The volume of ethanol was reduced and the solid amine hydroiodide salt was filtered and washed with ether. The solid obtained was dissolved in water and basified with 10% NaOH solution and extracted with ethyl acetate. The ethyl acetate layer was dried over Na2SO4 and concentrated to obtain the desired compound (4a) (4.37 g, 80%). m/z 280.9 (79Br) & 282.9 (81Br) (M+H)+.

Workup

  1. filtrationthe solid amine hydroiodide salt was filtered
  2. washwashed with ether
  3. customThe solid obtained
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5450043ae6db4eefa778df6410f74b12
Source dataset
uspto-grants-2015_07
Patent number
US09073942B2

Reaction notes

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