Water → N-(6-bromo-1,3-benzothiazol-2-yl)acetamide

HRID 2110788Notes

Reaction equation

HRID 2110788 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20].O>C1COCC1>[Br:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:19](=[O:21])[CH3:20])[S:3][C:4]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 851492-Benzothiazolamine, 6-bromo-

Product 1

HCID 3240669N-(6-bromo-1,3-benzothiazol-2-yl)acetamideYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-6-bromobenzothiazole (10 g, 43.65 mmol) and triethylamine (12.2 mL, 87.3 mmol) and N,N-dimethylaminopyridine (269 mg) in THF (100 mL) is added acetyl chloride (4.7 mL). After stirring for 17 hours water (100 mL) is added and the mixture is extracted twice with EtOAc (75 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford N-(6-bromo-benzothiazol-2-yl)-acetamide (8.79 g, 74%) as a solid.

Workup

  1. additionis added
  2. extractionthe mixture is extracted twice with EtOAc (75 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf2ed1b787494b3fa46e29710d165392
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

Loading…