Phenyl isocyanate → HCID 11603316, compound

HRID 493078Notes

Reaction equation

HRID 493078 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][C:5]2[CH:9]=[C:10]3[C:15](=[CH:16][C:4]=2[S:3]1(=[O:18])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11]3.C(N(CC)CC)C.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CS(C)=O>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]([C:33]([NH:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:34])[C:5]2[CH:9]=[C:10]3[C:15](=[CH:16][C:4]=2[S:3]1(=[O:17])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11]3

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 10730123HCID 10730123, compound

Product 1

HCID 11603316HCID 11603316, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1.3 g (5 mmol) 3,4-dihydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine 1,1-dioxide and 0.7 ml (5 mmol) triethylamine dissolved in 10 ml DMSO at room temperature was added 0.6 g (5 mmol) phenylisocyanate. After stirring for 20 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 1.9 g crude product. This material was recrystallized from ethanol followed by recrystallization from ethylacetate to give 0.7 g 3,4-dihydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine-4-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 1.9 g crude product
  7. customThis material was recrystallized from ethanol
  8. customfollowed by recrystallization from ethylacetate

Sources & evidence

ORD record
ord-8d689cf212b144ceb3b4401f2ae71fa3
Source dataset
uspto-grants-2009_05
Patent number
US07534787B2

Reaction notes

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