4-Toluenesulfonyl chloride → HCID 11053380, compound

HRID 893385Notes

Reaction equation

HRID 893385 reaction equation
C(N(CC)CC)C.[CH:8]([N:10]1[CH:14](C(O)=O)[CH2:13][S:12][CH:11]1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=O.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.Cl[C:36](=[CH2:39])[C:37]#[N:38]>ClCCl.O>[C:37]([C:36]1[CH:39]=[CH:8][N:10]2[C:14]=1[CH2:13][S:12][CH:11]2[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)#[N:38]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 701982-ChloroacrylonitrileHCID 10922588HCID 10922588, compound

Product 1

HCID 11053380HCID 11053380, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (4.67 g) is added to a suspension of 3-formyl-2-(3-pyridyl)-4-thiazolidinecarboxylic acid (10 g) in dichloromethane (15 cc) at a temperature close to 20° C. A clear light yellow solution is obtained. This solution is added dropwise in the course of 1 hour at 40° C. to a mixture of tosyl chloride (8.8 g) in dichloromethane (17 cc). The reaction mixture becomes homogeneous and orange-red in colour. 2-Chloroacrylonitrile (4.10 g) is then added quickly, followed, while the reaction medium is maintained at reflux, by triethylamine (9.37 g). The reaction mixture is maintained refluxing for a further 1 hour and 25 minutes. After cooling to room temperature, the reaction medium is hydrolysed with water (12 cc). The organic phase is decanted and the aqueous phase extracted with dichloromethane. The organic extracts are combined and dried overnight over sodium sulphate. After filtering, the solvent is evaporated under reduced pressure (20 mm Hg; 2.7 Pa) at 20° C. A crude product (11.11 g) is obtained, and is purified by chromatography on a column (diameter 4.5 cm) containing silica (100 g) (0.063-0.2 mm), eluting with a mixture of ethyl acetate and dichloromethane. 7-Cyano-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole (8.36g) is thereby obtained in the form of light beige-coloured crystals, m.p. 110° C. (yield 88.4% relative to the acid used).

Workup

  1. customclose to 20° C
  2. customA clear light yellow solution is obtained
  3. temperatureis maintained
  4. temperatureThe reaction mixture is maintained
  5. temperaturerefluxing for a further 1 hour and 25 minutes
  6. customThe organic phase is decanted
  7. extractionthe aqueous phase extracted with dichloromethane
  8. dry with materialdried overnight over sodium sulphate
  9. filtrationAfter filtering
  10. customthe solvent is evaporated under reduced pressure (20 mm Hg; 2.7 Pa) at 20° C
  11. customA crude product (11.11 g) is obtained
  12. customis purified by chromatography on a column (diameter 4.5 cm)
  13. additioncontaining silica (100 g) (0.063-0.2 mm)
  14. washeluting with a mixture of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-f6d8d9dbcd5841e493e2194611e420c6
Source dataset
uspto-grants-1992_06
Patent number
US05124459

Reaction notes

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