Triethylamine → 2-Fluoro-6-(3-oxo-pyrrolidine-1-sulfonyl)-benzonitrile

HRID 39226Notes

Reaction equation

HRID 39226 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[S:10](Cl)(=[O:12])=[O:11])#[N:2].Cl.[O:15]=[C:16]1[CH2:20][CH2:19][NH:18][CH2:17]1.C(N(CC)CC)C>O1CCCC1>[F:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([S:10]([N:18]2[CH2:19][CH2:20][C:16](=[O:15])[CH2:17]2)(=[O:12])=[O:11])[C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19106857Pyrrolidin-3-one hydrochlorideHCID 205052122-Cyano-3-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 442186612-Fluoro-6-(3-oxo-pyrrolidine-1-sulfonyl)-benzonitrileYield 15.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

110 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 5 ml of tetrahydrofuran are treated with 61 mg of 3-oxo-pyrrolidine hydrochloride and with 0.14 ml of triethylamine, and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo, the residue is solved in ethyl acetate and washed with a 1M HCl solution. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) affords 21 mg of 2-fluoro-6-(3-oxo-pyrrolidine-1-sulfonyl)-benzonitrile.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washwashed with a 1M HCl solution
  3. customPurification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-e2d1cdd8e0cb493a929b383643dbff70
Source dataset
uspto-grants-2013_09
Patent number
US08524896B2

Reaction notes

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