Acetic Anhydride → 2-Acetamido-5-bromo-1,3-thiazole

HRID 910290Notes

Reaction equation

HRID 910290 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.Br.[NH2:9][C:10]1[S:11][C:12]([Br:15])=[CH:13][N:14]=1.C(N(CC)CC)C.[OH-].[Na+]>ClCCl.O>[Br:15][C:12]1[S:11][C:10]([NH:9][C:5](=[O:7])[CH3:6])=[N:14][CH:13]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27238485-Bromothiazol-2-amine monohydrobromide

Product 1

HCID 3502602-Acetamido-5-bromo-1,3-thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.9 ml (42.3 mmol) of acetic anhydride are added to a solution of 10 g (38.5 mmol) of 2-amino-5-bromothiazole hydrobromide in 100 ml of dichloromethane and 11 ml (77 mmol) of triethylamine, cooled to 0° C. The reaction medium is stirred for 30 minutes at 0° C. and then for 18 hours at room temperature. After addition of water, the pH is adjusted to pH 8 with aqueous 1M sodium hydroxide solution and the reaction medium is extracted with dichloromethane. The dichloromethane phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is used in step b without purification.

Workup

  1. waitfor 18 hours at room temperature
  2. extractionthe reaction medium is extracted with dichloromethane
  3. dry with materialThe dichloromethane phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis used in step b without purification

Sources & evidence

ORD record
ord-4a25e5ee0d3d4512b0967e14f6614fc9
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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