Chloroform → (1,1-Dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

HRID 30989Notes

Reaction equation

HRID 30989 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][C:6]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[S:8](=[O:17])(=[O:16])[N:7]=1)C.C(Cl)(Cl)Cl>C1COCC1.Cl>[O:17]=[S:8]1(=[O:16])[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[NH:11][C:6]([CH2:5][C:4]([OH:18])=[O:3])=[N:7]1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 6588352H-1,2,4-Benzothiadiazine-3-acetic acid ethyl ester 1,1-dioxide

Product 1

HCID 11708529(1,1-Dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acidYield 85%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4c (1.98 g, 7.36 mmol) in THF (10 mL) and 6 N HCl (20 mL) was stirred for 2 days at room temperature. Chloroform (20 mL) was added to the solution to induce precipitation upon vigorous stirring 15 min. The precipitate was collected by vacuum filtration to give 10b (1.50 g, 85%) as a yellow solid. 1H NMR (400 MHz, D6-DMSO) δ 12.25 (s, 1 H), 7.78 (d, J=8 Hz, 1 H), 7.66 (td, J=8, 1 Hz, 1 H), 7.44 (td, J=8, 1 Hz, 1 H), 7.32 (d, J=8 Hz, 1 H), 3.70 (br s, 1 H), 3.58 (s, 2 H).

Workup

  1. customprecipitation
  2. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-202f7ccc55c848eb8c8253a1b259f983
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

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