Ethyl 3-[2-(aminosulfonyl)anilino]-3-oxopropanoate → 2H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxide

HRID 30988Notes

Reaction equation

HRID 30988 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15](=[O:18])(=[O:17])[NH2:16])=O)[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15](=[O:18])(=[O:17])[N:16]=1)[CH3:2]

Participants

3

Reactant 1

HCID 14674447Ethyl 3-[2-(aminosulfonyl)anilino]-3-oxopropanoate

Product 1

HCID 6588352H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxideYield 85%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 12 (2.50 g, 8.73 mmol) in phosphorous oxychloride (50 mL) was heated under reflux for 6 h, cooled to room temperature, and concentrated in vacuo. The residue was dissolved in ethyl acetate (200 mL) and extracted with saturated Na2CO3 (100 mL). The organic layer was washed with 1 N HCl (50 mL), dried over MgSO4, and concentrated in vacuo to give 4c (1.99 g, 85%) as a yellow solid. 1H NMR (400 MHz, D6-DMSO) δ 12.22 (s, 1H), 7.79 (d, J=12 Hz, 1 H), 7.67 (t, J=10 Hz, 1 H), 7.45 (t, J=8 Hz, 1 H), 7.30 (d, J=8 Hz, 1 H), 4.15 (dt, J=7.2, 7.2 Hz, 2H), 3.69 (s, 2 H), 1.21 (t, J=7.2 Hz, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. extractionextracted with saturated Na2CO3 (100 mL)
  6. washThe organic layer was washed with 1 N HCl (50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e978b5fe462b4d8d8f3fe02ec8e5c2a2
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

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