4-Bromo-2-iodoaniline → Benzothiazole, 6-bromo-2-methyl-

HRID 1270893

Reaction equation

HRID 1270893 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4](I)[CH:3]=1.[CH3:10][C:11](N)=[S:12]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:11]([CH3:10])[S:12][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 8239344-Bromo-2-iodoanilineHCID 2723949Thioacetamide

Product 1

HCID 138448Benzothiazole, 6-bromo-2-methyl-Yield 48.2%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-2-iodo-phenylamine (1.5 g, 5.0 mmol), thiacetamide (381 mg, 5.0), cupric oxide (280 mg, 3.5 mmol), dppf (56 mg, 0.10 mmol), Pd2(dba)3 (48 mg, 0.052 mmol) in DMF was heated at 60° C. for 1 hour, cooled to room temperature, partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and concentrated. The concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride to give 550 mg (40% yield) of the desired product. MS (ESI(+)) m/e 227.8, 229.8 (M+H)+.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride

Sources & evidence

ORD record
ord-336ac4bd754845cdb389cffd63b7f993
Source dataset
uspto-grants-2007_04
Patent number
US07202363B2

Linked notes

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