Triethylamine → HCID 54574468, compound

HRID 1289361Notes

Reaction equation

HRID 1289361 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): δ7.21 (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-e5646d1b7c9f411ebdc864c604cc687f
Source dataset
uspto-grants-1998_05
Patent number
US05750471

Reaction notes

Loading…