N-Iodosuccinimide → HCID 58017974, compound

Temperature

50 °C

5.30 g (26.0 mmol) of 2-chloro-4-hexylthiazole and 7.02 g (31.2 mmol) of N-iodosuccinimide were dissolved in 40 mL of acetonitrile, and stirred for 2 hours at 50° C. under argon gas purge. The resultant reaction mixed liquid was washed with a Na2S203 aqueous solution, and the aqueous layer was extracted with chloroform and added to the organic layer. The organic layer was concentrated, and subjected to silica gel column chromatography (development solvent:chloroform/hexane=1/1 (volumetric ratio)) to take out red transparent liquid. Since a peak of a molecular weight of 330 containing one chlorine atom was observed in the mass spectrum (apparatus: HP-6890GC/HP-5973MSD, column: SGE BPX-5 (30 m×0.25 mm I.D.×025 μm), column temperature: 50° C. (5 minutes)→10° C./min.→350° C. (held for 5 minutes), injection port temperature: 280° C., carrier gas: He, 1.0 ml/min.), it could be confirmed that the above-described red transparent liquid was the intended 2-chloro-4-hexyl-5-iodothiazole. The amount obtained was 7.50 g, and the yield was 87.6%.

1. custompurge
2. customThe resultant reaction
3. additionmixed liquid
4. washwas washed with a Na2S203 aqueous solution
5. extractionthe aqueous layer was extracted with chloroform
6. additionadded to the organic layer
7. concentrationThe organic layer was concentrated
8. additionSince a peak of a molecular weight of 330 containing one chlorine atom
9. customwas observed in the mass spectrum (apparatus: HP-6890GC/HP-5973MSD, column: SGE BPX-5 (30 m×0.25 mm I.D.×025 μm), column temperature: 50° C. (5 minutes)→10° C./min.→350° C. (held for 5 minutes), injection port temperature: 280° C., carrier gas: He, 1.0 ml/min.), it
10. customThe amount obtained

ORD record

ord-8d31e06b5e6f4daeb85de1577a43c333

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940856B2