Triethylamine → HCID 69357218, compound

HRID 852584Notes

Reaction equation

HRID 852584 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[C:10]([F:22])=[C:11]([CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:7])=[O:6].CCN(CC)CC>CCO>[O:6]=[S:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][N:8]1[C:9]1[C:10]([F:22])=[C:11]([CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 69359115HCID 69359115, compound

Product 1

HCID 69357218HCID 69357218, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 3-{[(3-chloropropyl)sulfonyl]amino}-2-fluoro-5-nitrobenzoate (D145) (300 mg, 0.85 mmol, 1 equiv) in EtOH (30 ml) was added NEt3 (280 μl, 2 mmol, 2.3 equiv) and the resulting solution was refluxed for 1.5 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. The residue was triturated with AcOEt/Et2O to give methyl 3-(1,1-dioxido-2-isothiazolidinyl)-2-fluoro-5-nitrobenzoate (D147) (150 mg, 55%) as a light tan solid which was used in the next step without further purification. [M+H+ NH3]+=336.3, RT=2.50 min.

Workup

  1. temperaturethe resulting solution was refluxed for 1.5 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic phase was washed with a 2N aqueous HCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with AcOEt/Et2O

Sources & evidence

ORD record
ord-22176951b3f34cb3a6653d5c4f24cde0
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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