Hydrochloric Acid → 7-Bromo-1,3-benzothiazol-2-amine

HRID 2077517Notes

Reaction equation

HRID 2077517 reaction equation
[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11]C(=O)C)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.BrC1C=CC2N=C(NC(=O)C)SC=2C=1.[OH-].[Na+].Cl>CO.O>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH2:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3240669N-(6-bromo-1,3-benzothiazol-2-yl)acetamideHCID 57584914N-(7-bromobenzo[d]thiazol-2-yl)acetamide

Product 1

HCID 203571127-Bromo-1,3-benzothiazol-2-amineYield 116%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture (562 mg, 2.07 mmol) of N-(7-bromobenzo[d]thiazol-2-yl)acetamide and N-(6-bromobenzo[d]thiazol-2-yl)acetamide were suspended in MeOH (10 mL) and water (2 mL), sodium hydroxide (468.1 mg, 11.70 mmol) were added. The flask was fit with a reflux condenser and placed in a preheated oil bath (78° C.-80° C.) and stirred under nitrogen for 90 minutes. The reaction was cooled to RT and treated with 5N HCl to lower the pH to about 2. The suspension was filtered, and the solid was washed with water. The filtrate was treated with saturated sodium bicarbonate to adjust pH to about 7, and it was filtered again. The solid was collected and purified on an HPLC (10-95% MeCN/water with 0.1% TFA over 40 minutes) to provide 7-bromobenzo[d]thiazol-2-amine (550.3 mg).

Workup

  1. customThe flask was fit with a reflux condenser
  2. customplaced in a preheated oil bath
  3. filtrationThe suspension was filtered
  4. washthe solid was washed with water
  5. additionThe filtrate was treated with saturated sodium bicarbonate
  6. filtrationwas filtered again
  7. customThe solid was collected
  8. custompurified on an HPLC (10-95% MeCN/water with 0.1% TFA over 40 minutes)

Sources & evidence

ORD record
ord-94550ed8be4c49288e6dd6ac49e2d858
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…