Acetic Acid → HCID 19836752, compound

HRID 1521852Notes

Reaction equation

HRID 1521852 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=O)[CH2:2]1.C[C:13]([CH3:16])([O-:15])C.[K+].[C:18]([OH:21])(=O)[CH3:19].[CH3:22][N:23](C=O)C>O>[CH:22]1[N:4]2[C:3]([CH2:2][S:1][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=32)=[C:19]([C:18]([O:15][CH2:13][CH3:16])=[O:21])[N:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228Dimethylformamide2×HCID 213964H-1,4-Benzothiazin-3-oneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 19836752HCID 19836752, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2H-1,4-benzothiazin-3(4H)-one (0.7 g, 4.24 mmol, 1 eq) in DMF (20 mL) is added potassium tert- butoxide (0.50 g, 4.49 mmol, 1.06 eq) and the reaction mixture is stirred at RT for 10 min. The reaction mixture is cooled with ice and diethyl chloro phosphonate (1.1 mL, 7.63 mmol, 1.8 eq) is added and the reaction mixture is stirred at RT for 5 minutes. The reaction mixture is then cooled with ice and a solution of ethyl isocyano acetate (0.65 mL, 5.94 mmol, 1.4 eq) in DMF and potassium tert-butoxide (0.66 g, 5.93 mmol, 1.4 eq) are sequentially added and the reaction mixture is stirred at RT overnight. The reaction mixture is acidified with 10 mL of acetic acid, diluted with water and poured into ice and extracted with ethylacetate. The organic layer is dried over Na2SO4 and concentrated. The crude is purified by column chromatography to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 8.50 (s, 1H), 7.90-7.88 (d, J=7.3 Hz, 1H), 7.56-7.54 (m, 1H), 7.39-7.36 (m, 1H), 7.32-7.30 (m, 1H), 4.42 (s, 2H), 4.27 (q, J=7.7 Hz, 2H), 1.29 (t, J=6.6 Hz, 3H). MS (ESI+): 261.2. HPLC (max plot) 95.13%; Rt 3.62 min.

Workup

  1. additionis added
  2. stirringthe reaction mixture is stirred at RT for 5 minutes
  3. temperatureThe reaction mixture is then cooled with ice
  4. stirringthe reaction mixture is stirred at RT overnight
  5. additionpoured into ice
  6. extractionextracted with ethylacetate
  7. dry with materialThe organic layer is dried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude is purified by column chromatography

Sources & evidence

ORD record
ord-144344f1c2d84b1cb69b412e217975c2
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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