Bromine → 2-Amino-1,3-benzothiazole-7-carboxylic acid

HRID 57232Notes

Reaction equation

HRID 57232 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])[C:2]([NH2:4])=[S:3].BrBr>C(Cl)(Cl)Cl>[NH2:4][C:2]1[S:3][C:6]2[C:7]([C:8]([OH:10])=[O:9])=[CH:11][CH:12]=[CH:13][C:5]=2[N:1]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 8205751-(3-Carboxyphenyl)-2-thiourea

Product 1

HCID 202855902-Amino-1,3-benzothiazole-7-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 3-thioureidobenzoic acid (1.06 g, 5.41 mmol) in chloroform (25 mL) was added a solution of bromine (0.4 mL, 8.0 mmol) dropwise at room temperature. The resulting mixture was heated under reflux for 3 hrs and allowed to stir at room temperature for 60 hrs. The solvent was evaporated, water was added and the resulting solids were isolated by filtration. The crude product was washed with water and dried to yield 1.03 g (98%) of the title compound as a gray solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hrs
  3. customThe solvent was evaporated
  4. additionwater was added
  5. customthe resulting solids were isolated by filtration
  6. washThe crude product was washed with water
  7. customdried

Sources & evidence

ORD record
ord-d5738553286a4b90ad48a73995b7d455
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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