Acetic Anhydride → N-(5-Bromo-thiazol-2-yl)-N-pyridin-2-yl-acetamide

HRID 1355433Notes

Reaction equation

HRID 1355433 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][CH:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[Br:1][C:2]1[S:6][C:5]([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:14](=[O:16])[CH3:15])=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 53294005-bromo-N-(pyridin-2-yl)thiazol-2-amine

Product 1

HCID 18506782N-(5-Bromo-thiazol-2-yl)-N-pyridin-2-yl-acetamide

Conditions

Temperature
100 °C

Procedure

To a flask containing (5-Bromo-thiazol-2-yl)-pyridin-2-yl-amine (5-4, 4.58 g, 17.9 mmol was added 30 mL acetic anhydride. The suspension was then heated to 100° C. After about 1.5 hours, the acetic anhydride and acetic acid was removed under reduced pressure, heating the bath to 70° C. Two 70 mL portions of toluene were also added for azeotropic distillation. The product was obtained as a tan colored precipitate. 1H NMR (DMSO-d6): δ8.65 (d, 1H, J=3.9 Hz), 8.09 (t, 1H, J=8.6 Hz), 7.67 (d, 1H, J=8 Hz), 7.59 (t, 1H, J=6.6 Hz), 7.47 (s, 1H). mp 132-138° C.

Workup

  1. customthe acetic anhydride and acetic acid was removed under reduced pressure
  2. temperatureheating the bath to 70° C
  3. additionTwo 70 mL portions of toluene were also added for azeotropic distillation
  4. customThe product was obtained as a tan colored precipitate

Sources & evidence

ORD record
ord-215b4b16411144859a520b07257e75d4
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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