Acetic Acid → HCID 20377628, compound

HRID 717778Notes

Reaction equation

HRID 717778 reaction equation
N([N:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][CH2:5][CH2:4]1)=O.C([O-])(O)=O.[Na+].[C:18](O)(=O)[CH3:19]>[Zn]>[CH3:4][N:3]1[CH2:19][CH2:18][C:12]2[N:3]3[CH2:4][CH2:5][S:6][C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([C:8]3=4)[C:7]=2[CH2:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 218596124-nitroso-3,4-dihydro-2H-benzo[b][1,4]thiazine

Product 1

HCID 20377628HCID 20377628, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
95 °C

Procedure

4-Nitroso-3,4-dihydro-2H-benzo[1,4]thiazine (1 g, 5.55 mmol) was dissolved in acetic acid (25 mL) and N-Me- piperidone (753 mg, 6.66 mmol) and zinc dust (1.8 g, 27.77 mmol) was added portionwise at RT. The reaction mixture was heated at 95° C. for 2 h. After completion of reaction, the mixture was basified with NaHCO3 and extracted with EtOAc, dried over sodium sulfate and concentrated under vacuum to obtain product. 1H NMR (CD3OD, Formate Salt): d (ppm): 7.20 (d, 1H), 6.98 (t, 1H), 6.90 (d, 1H), 4.32 (t, 2H), 4.28 (s, 2H), 3.50 (t, 2H), 3.30 (m, 2H), 3.10 (t, 2H), 2.98 (s, 3H).

Workup

  1. customAfter completion of reaction
  2. extractionextracted with EtOAc
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto obtain product

Sources & evidence

ORD record
ord-e66cec5f291e45129b38c2c48687c02a
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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