Iodobenzene → HCID 23317473, compound

HRID 1982177Notes

Reaction equation

HRID 1982177 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:14](=[O:15])[CH2:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[S:10]1.C([O-])(=O)C.[K+].I[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3].[O-2].[Ba+2]>C1(C)C=C(C)C=C(C)C=1.[Cu]>[C:26]1([CH:13]2[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[C:14]2=[O:15])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 11575IodobenzeneHCID 517044Potassium AcetateHCID 9855530Barium Oxide Nanoparticle DispersionHCID 9989226AluminaHCID 23317447HCID 23317447, compound

Product 1

HCID 23317473HCID 23317473, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7947MesityleneSolvent

Procedure

2.7 g of 2,3-dihydro-2-(2-methoxyphenyl)benzothiazin-3-one, together with 1.2 g of potassium acetate, 6 g of iodobenzene and copper on an aluminum oxide support as the catalyst, in 80 ml of mesitylene are heated at 160° C. for 6 hours under a water separator which is charged with 2 g of barium oxide and 5 g of silica gel. After filtration, the residue is washed with dilute ammonia, and the filtrate is concentrated and chromatographed on 100 g of silica gel using ispropyl ether. 2.6 g of crude product are obtained, and this crystallizes from isopropyl ether/a little acetone, melting point 133° C.

Workup

  1. filtrationAfter filtration
  2. washthe residue is washed with dilute ammonia
  3. concentrationthe filtrate is concentrated
  4. customchromatographed on 100 g of silica gel using ispropyl ether

Sources & evidence

ORD record
ord-660a895ded4544a1bc328bdc38619672
Source dataset
uspto-grants-1986_06
Patent number
US04595685

Reaction notes

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