Triethylamine → HCID 11053380, compound

HRID 893384Notes

Reaction equation

HRID 893384 reaction equation
[CH:1]([N:3]1[CH:7](C(O)=O)[CH2:6][S:5][CH:4]1[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=O.C(N(CC)CC)C.CS(Cl)(=O)=O.Cl[C:30](=[CH2:33])[C:31]#[N:32]>ClCCl.O>[C:31]([C:30]1[CH:33]=[CH:1][N:3]2[C:7]=1[CH2:6][S:5][CH:4]2[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)#[N:32]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 701982-ChloroacrylonitrileHCID 10922588HCID 10922588, compound

Product 1

HCID 11053380HCID 11053380, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

3-Formyl-2-(3-pyridyl)-4-thiazolidinecarboxylic acid (10 g) is suspended in dichloromethane (15 cc) in a 50 cc three-necked flask equipped with a condenser, a dropping funnel, a magnetic stirrer, a thermometer and a gas-holder. Then triethylamine (4.8 g) is added at 20° C. A homogeneous colourless solution is obtained. This solution is added dropwise in the course of 50 minutes and at 25° C. to a stirred mixture of methanesulphonyl chloride (5.29 g) and dichloromethane (17 cc). 2-Chloroacrylonitrile (4.04 g) is then added quickly, followed at 20°-35° C. and over the course of one hour, by triethylamine (9.35 g) and dichloromethane (5 cc). The mixture is then refluxed for 50 minutes. After cooling, it 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 off under reduced pressure 20 mm Hg; 2.7 kPa) at 20° C. A crude product (9 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 (7.10 g) is thereby obtained in the form of light beige-coloured crystals m.p. 108° C. (yield 82.5% relative to the acid used).

Workup

  1. customequipped with a condenser, a dropping funnel, a magnetic stirrer
  2. customA homogeneous colourless solution is obtained
  3. temperatureThe mixture is then refluxed for 50 minutes
  4. temperatureAfter cooling
  5. customThe organic phase is decanted
  6. extractionthe aqueous phase extracted with dichloromethane
  7. dry with materialdried overnight over sodium sulphate
  8. filtrationAfter filtering
  9. customthe solvent is evaporated off under reduced pressure 20 mm Hg
  10. customat 20° C
  11. customA crude product (9 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-677fcbdb1dd34c618fd7fe1908a3186a
Source dataset
uspto-grants-1992_06
Patent number
US05124459

Reaction notes

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