Hydrochloric Acid → Maleimide, N-(p-chlorophenyl)-

HRID 1784042Notes

Reaction equation

HRID 1784042 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](/[CH:11]=[CH:12]\[C:13]([OH:15])=O)=[O:10])=[CH:4][CH:3]=1.C[Si](N[Si](C)(C)C)(C)C.Cl>C1C=CC=CC=1.[Cl-].[Cl-].[Zn+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9](=[O:10])[CH:11]=[CH:12][C:13]2=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 5356193AF-794/00086051

Product 1

HCID 15400Maleimide, N-(p-chlorophenyl)-Yield 97%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

In Analogy to the procedure given in Mhaske et al., Synthesis, 2003, p863-870: A solution of 65 g (288 mmol) of (Z)-3-(4-chloro-phenylcarbamoyl)-acrylic acid in 300 ml of benzene was treated with 41.2 g (302 mmol) of zinc dichloride, dropwise with 90.1 ml (432 mmol) of bis(trimethylsilyl)amine and refluxed during 5 hrs. The mixture was poured into 300 ml of aqueous HCl (0.5 M). The aqueous phase was extracted with AcOEt, the combined organic phases were washed successively with saturated aqueous NaHCO3 and brine, and finally dried over Na2SO4. Evaporation of the solvent gave 58 g (97%) of the title compound. Brown amorphous solid. MS: 208 (M+H)+.

Workup

  1. customIn Analogy to the procedure given in Mhaske et al., Synthesis, 2003, p863-870
  2. temperaturerefluxed during 5 hrs
  3. extractionThe aqueous phase was extracted with AcOEt
  4. washthe combined organic phases were washed successively with saturated aqueous NaHCO3 and brine
  5. dry with materialfinally dried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-befc109c4e5b4818a83415c21aacd7d1
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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