3-Chloropropanesulphonyl chloride → 3-(1,1-Dioxido-2-isothiazolidinyl)benzonitrile

HRID 1991428Notes

Reaction equation

HRID 1991428 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Cl[CH2:11][CH2:12][CH2:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl.CCN(C(C)C)C(C)C>[O:15]=[S:14]1(=[O:16])[CH2:13][CH2:12][CH2:11][N:1]1[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 167023-Aminobenzonitrile

Product 1

HCID 246913383-(1,1-Dioxido-2-isothiazolidinyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

1 g of 3-Aminobenzonitril were dissolved in 10 ml DCM and 2.2 ml of DIPEA. 1.3 ml of 3-Chloro-propane-1-sulfonyl chloride were added and the reaction mixture stirred at rt overnight. The organic layer was evaporated, the crude taken up in DMF and 1.5 ml DBU added. The reaction mixture was stirred at rt overnight. DCM was added and the organic phase washed with water. The organic layer was separated, dried over Na2SO4 and evaporated. MS(ISO): 232.2 (MH+)

Workup

  1. customThe organic layer was evaporated
  2. addition1.5 ml DBU added
  3. stirringThe reaction mixture was stirred at rt overnight
  4. additionDCM was added
  5. washthe organic phase washed with water
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-4d3055f90e884a71b3f55ad17c8eb513
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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