Triethylamine → HCID 69492303, compound

HRID 493076Notes

Reaction equation

HRID 493076 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) triethylamine 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-9598d98fadf4435d9ee79a744b6b8c64
Source dataset
uspto-grants-2009_05
Patent number
US07534787B2

Reaction notes

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