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

HRID 216260

Reaction equation

HRID 216260 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-31a0b31931a844cf9ba68387e50535f3
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Linked notes

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