Thiazolidine → 2-Fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile

HRID 39224

Reaction equation

HRID 39224 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].[S:14]1[CH2:18][CH2:17][NH:16][CH2:15]1>O1CCCC1>[F:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([S:10]([N:16]2[CH2:17][CH2:18][S:14][CH2:15]2)(=[O:12])=[O:11])[C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 10444ThiazolidineHCID 205052122-Cyano-3-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 442186552-Fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

440 mg of 2-cyano-3-fluoro-benzenesulfonyl chloride in 10 ml of tetrahydrofuran are treated with 0.36 ml of thiazolidine and the mixture is stirred for 16 hours at room temperature. The reaction mixture is concentrated in vacuo. Purification by Flash chromatography (eluent: cyclohexane/ethyl acetate 1:1) followed by acidic washing with a 1M HCl solution affords 318 mg of 2-fluoro-6-(thiazolidine-3-sulfonyl)-benzonitrile.

Workup

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

Sources & evidence

ORD record
ord-62d17e228e394a5fafc800d9e62ffeab
Source dataset
uspto-grants-2013_09
Patent number
US08524896B2

Linked notes

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