Triethylamine → HCID 54574468, compound

HRID 363293Notes

Reaction equation

HRID 363293 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([NH2:15])=[C:6]2[C:10]=1[N:9]([CH2:11][CH3:12])[S:8](=[O:14])(=[O:13])[CH2:7]2.[O:17]=[C:18](Cl)OC(Cl)(Cl)Cl.C(N(CC)CC)C>O1CCOCC1>[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH3:12])[S:8](=[O:14])(=[O:13])[CH2:7][C:6]=2[C:5]([N:15]=[C:18]=[O:17])=[C:4]([F:16])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 53662361HCID 53662361, compound

Product 1

HCID 54574468HCID 54574468, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 7-chloro-1-ethyl-5-fluoro-1,3-dihydro-2,1-benzisothiazol-4-amine-2,2-dioxide (1.30 g, 4.91 mmol), diphosgene (1.17 g, 1.2 eq) in p-dioxane (20 mL), triethylamine (0.6 g, 1.2 eq) was added and the resulting reaction mixture was heated at reflux for overnight. The precipitated triethylamine hydrochloride was filtered off and the solvents were removed in vacuo and dried to give the title compound of Step A as a brown semisolid. 1H NMR (CDCl3, 400 MHz): δ 7.21 (d,1H, J=9.5 Hz), 4.28 (s,2H), 3.94 (q,2H), 1.22 (t,3H, J=7.5 Hz).

Workup

  1. additionwas added
  2. customthe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for overnight
  5. filtrationThe precipitated triethylamine hydrochloride was filtered off
  6. customthe solvents were removed in vacuo
  7. customdried

Sources & evidence

ORD record
ord-18dd9f2c813345529f84765316ac986a
Source dataset
uspto-grants-1999_02
Patent number
US05874382

Reaction notes

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