2-Thiazoline → HCID 67802610, compound

HRID 1900752Notes

Reaction equation

HRID 1900752 reaction equation
Br[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[S:18]1[CH2:22][CH2:21][N:20]=[CH:19]1>>[CH3:15][C:13]1[CH:14]=[C:5]2[CH2:4][CH:3]([CH2:2][CH:19]3[N:20]=[CH:21][CH2:22][S:18]3)[O:17][C:6]2=[C:7]2[C:12]=1[NH:11][C:10](=[O:16])[CH:9]=[CH:8]2

Participants

3

Reactant 2

HCID 1202692-ThiazolineHCID 233696452-Bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 67802610HCID 67802610, compoundYield 38.4%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-bromomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (4.802 g) and thiazoline (5.815 g) was stirred at 150° C. in the stream of argon gas for 4 hours. The solvent was distilled off under reduced pressure. Chloroform was added to the residue, and extracted with 1N-HCl. After the extract was washed with chloroform, 1N-NaOH was added to bring the pH basic. Extraction was performed with chloroform, followed by washing with water. After dried, the residue was crystallized from methanol to obtain 1.885 g of a free base of the title compound as pale yellow powder (mp.: 196°-199° C.).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionChloroform was added to the residue
  3. extractionextracted with 1N-HCl
  4. washAfter the extract was washed with chloroform, 1N-NaOH
  5. additionwas added
  6. extractionExtraction
  7. washby washing with water
  8. customAfter dried
  9. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-0c66a32771b7449b98958c3b792b3d13
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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