Triethylamine → HCID 69492303, compound

HRID 746372Notes

Reaction equation

HRID 746372 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[C:14](=[O:15])[CH2:13][C:12]2[CH:16]=[C:17]3[C:22](=[CH:23][C:11]=2[S:10]1(=O)=O)[CH2:21][CH2:20][CH2:19][CH2:18]3.FC1C=CC(N=C=O)=CC=1>CS(C)=O>[CH3:8][N:9]1[C:14](=[O:15])[CH2:13][C:12]2[CH:16]=[C:17]3[C:22](=[CH:23][C:11]=2[S:10]1)[CH2:21][CH2:20][CH2:19][CH2:18]3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 68838836HCID 68838836, compound

Product 1

HCID 69492303HCID 69492303, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.76 g (7.5 mmol) triethylamin were added to a solution of 2 g (7.5 mmol) 3,4,6,7,8,9-hexahydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine 1,1-dioxide and 1.03 g (7.5 mmol) p-fluor-phenylisocyanate dissolved in 50 mL DMSO (dimethyl sulfoxide) at room temperature. After stirring for 1 hr the resulting mixture was quenched with dilute HCl in an ice bath and then extracted with ether (2 times). The combined ether extracts were washed, dried and concentrated to give 2.3 g crude product. This material was recrystallized from ethanol to give 1.7 g 3,4,6,7,8,9-hexahydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine-4-(4-fluor)carboxanilide 1,1-dioxide.

Workup

  1. customwas quenched with dilute HCl in an ice bath
  2. extractionextracted with ether (2 times)
  3. washThe combined ether extracts were washed
  4. customdried
  5. concentrationconcentrated
  6. customto give 2.3 g crude product
  7. customThis material was recrystallized from ethanol

Sources & evidence

ORD record
ord-b1afb0f4428f437cabf6eb3a5de695a3
Source dataset
uspto-grants-2008_07
Patent number
US07393843B2

Reaction notes

Loading…