Phenyl isocyanate → HCID 11515843, compound

HRID 746376Notes

Reaction equation

HRID 746376 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[CH2:8][C:7]2[S:11][C:12]([CH3:14])=[CH:13][C:6]=2[S:5]1(=[O:16])=[O:15].[H][H].[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[CH3:3][N:4]1[C:9](=[O:10])[CH:8]([C:26]([NH:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:27])[C:7]2[S:11][C:12]([CH3:14])=[CH:13][C:6]=2[S:5]1(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 10585618HCID 10585618, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11515843HCID 11515843, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 0.78 g (32.5 mmol) sodium hydride in 50 mL tetrahydrofurane was added at −5° C. under N2 a solution of 5 g (21.6 mmol) 3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide in 50 mL tetrahydrofurane. After termination of the hydrogen formation 6.5 g (55 mmol) phenylisocyanate dissolved in 50 mL tetrahydrofurane were added at −5° C. After stirring at room temperature the resulting mixture was quenched with ice/water and by addition of dilute HCl and then extracted with CH2Cl2 (2 times). The combined CH2Cl2 extracts were washed, dried and concentrated to give 6 g crude product. This material was recrystallized from ethanol to give 5.2 g 3,4-dihydro-2,6-dimethyl-3-oxo-2H-thieno[2,3-e]-1,2-thiazine-4-carboxanilide 1,1-dioxide.

Workup

  1. additionwere added at −5° C
  2. customwas quenched with ice/water and by addition of dilute HCl
  3. extractionextracted with CH2Cl2 (2 times)
  4. washThe combined CH2Cl2 extracts were washed
  5. customdried
  6. concentrationconcentrated
  7. customto give 6 g crude product
  8. customThis material was recrystallized from ethanol

Sources & evidence

ORD record
ord-bb47f0fa941449e9aa35cc2ceb66f5ae
Source dataset
uspto-grants-2008_07
Patent number
US07393843B2

Reaction notes

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