Triethylamine → N-[4-(4-Oxo-4H-1,3-benzothiazin-2-yl)phenyl]acetamide

HRID 1442598Notes

Reaction equation

HRID 1442598 reaction equation
[C:1]([NH:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([S:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C([N:25](CC)CC)C.ClC(OCC)=O.[N-]=[N+]=[N-].[Na+].C(P(CCCC)CCCC)CCC>CC(C)=O.O>[O:15]=[C:14]1[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[S:11][C:9]([C:8]2[CH:21]=[CH:22][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)=[N:25]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13831TributylphosphineHCID 33557Sodium AzideHCID 586101152-{[4-(Acetylamino)benzoyl]thio}benzoic acid

Product 1

HCID 10447270N-[4-(4-Oxo-4H-1,3-benzothiazin-2-yl)phenyl]acetamideYield 29%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

2-{[4-(Acetylamino)benzoyl]thio}benzoic acid (1.10 g, 3.5 mmol) was suspended in acetone (10 ml). While stirring under ice cooling, triethylamine (0.50 g, 4.9 mmol) and then ethyl chloroformate (0.53 g, 3.8 mmol) were dropwise added to the suspension. After stirring at the same temperature for an hour, an aqueous solution (10 ml) of sodium azide (0.34 g, 5.2 mmol) was dropwise added to the reaction mixture, followed by further stirring for an hour. The reaction mixture was diluted with water and the dilution was extracted with toluene (100 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and then filtered. The toluene solution was cooled to about −10° C. and tributylphosphine (0.85 g, 4.2 mmol) was dropwise added to the solution. After completion of the dropwise addition, the reaction temperature was reverted to room temperature and the mixture was heated under reflux for 15 minutes. The reaction solution was concentrated under reduced pressure and washed with isopropyl ether. Then, the residue was recrystallized from tetrahydrofuran-ethanol to give the title compound (0.30 g, 29%) as crystals.

Workup

  1. stirringAfter stirring at the same temperature for an hour
  2. stirringby further stirring for an hour
  3. extractionthe dilution was extracted with toluene (100 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. additionAfter completion of the dropwise addition
  8. customwas reverted to room temperature
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 15 minutes
  11. concentrationThe reaction solution was concentrated under reduced pressure
  12. washwashed with isopropyl ether
  13. customThen, the residue was recrystallized from tetrahydrofuran-ethanol

Sources & evidence

ORD record
ord-3fe93788a58747a88081764df84fb5a5
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

Loading…