Acetic Anhydride → N-(7-Oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide

HRID 1807676Notes

Reaction equation

HRID 1807676 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[O:11]=[C:10]1[C:4]2[S:3][C:2]([NH:1][C:12](=[O:14])[CH3:13])=[N:6][C:5]=2[CH2:7][CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

Product 1

HCID 597793N-(7-Oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide

Procedure

To acetic anhydride (80 mL) was added at rt 2-amino-5,6-dihydro-4H-benzothiazol-7-one (10 g, 59.4 mmol) and the yellow suspension was heated to reflux. After 1.75 h stirring at this temperature, the RM was allowed to cool with stirring, and stirred overnight at rt. After further cooling with an ice/NaCl bath, the suspension was filtered. The solid was then refluxed twice with acetone (10 mL then 15 mL) and filtered. The resulting solid was dried under vacuum at 40° C. overnight to afford the title compound as a beige solid (HPLC: tR 3.47 min (Method A3), M−H=211.1), 1H-NMR in DMSO-d6 (600 MHz): 12.55 (s, br, 1H); 2.84 (t, 2H); 2.48 (t, 2H); 2.17 (s, 3H); 2.065 (qt, 2H)).

Workup

  1. temperaturethe yellow suspension was heated to reflux
  2. temperatureto cool
  3. stirringwith stirring
  4. stirringstirred overnight at rt
  5. temperatureAfter further cooling with an ice/NaCl bath
  6. filtrationthe suspension was filtered
  7. temperatureThe solid was then refluxed twice with acetone (10 mL
  8. filtration15 mL) and filtered
  9. customThe resulting solid was dried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-b5afd799b3f445e98448b51c0ec76255
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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