Acetone → HCID 86691928, compound

HRID 717775Notes

Reaction equation

HRID 717775 reaction equation
[N:1]([N:3]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2)=O.[Cl-].[NH4+].O.[CH3:22][C:23]([CH3:25])=O>[Zn]>[CH3:22][C:23](=[N:1][N:3]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2)[CH3:25]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 25517Ammonium ChlorideHCID 86691929HCID 86691929, compound

Product 1

HCID 86691928HCID 86691928, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
-5 °C

Procedure

To a solution of 4-nitroso-2-(pyridin-4-yl)-3,4-dihydro-2H-benzo[b][1,4]thiazine (0.3 g, 0.00116 mol) in acetone (12 mL) was added saturated ammonium chloride solution (3 mL) and water (3 mL) at RT, and the resulting brown colored reaction mixture was cooled to −5° C. Zinc dust (0.15 g, 0.00233 mol) was added portionwise at the same temperature and stirred for 10 min. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure and extracted with EtOAc (3×50 mL). The organic layer was dried over anhydrous sodium sulfate, solvent was removed under reduced pressure to obtain product as a brown colored oil (0.25 g).

Workup

  1. customAfter completion of reaction (monitored by TLC), solvent
  2. customwas removed under reduced pressure
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate, solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-eb07514533c443ad81a9886c28de36e4
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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