Bromine → 2-Amino-5-methoxy-1,3-benzothiazole-7-carboxylic acid

HRID 712279Notes

Reaction equation

HRID 712279 reaction equation
BrBr.[C:3]([NH:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1)[C:10]([OH:12])=[O:11])(=[S:5])[NH2:4]>C(Cl)(Cl)Cl>[NH2:4][C:3]1[S:5][C:8]2[C:9]([C:10]([OH:12])=[O:11])=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 866639913-(Carbamothioylamino)-5-methoxy-benzoic acid

Product 1

HCID 866639922-Amino-5-methoxy-1,3-benzothiazole-7-carboxylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (56 μl, 1.09 mmol) was added to a suspension of 3-(carbamothioylamino)-5-methoxy-benzoic acid (248 mg, 1.09 mmol) in chloroform (7 mL). The reaction was stirred at ambient temperature resulting in large granules of solid material which were pulverized with a spatula. The chloroform was removed by pipette and the remaining solid was triturated with dichloromethane to give the product as a pale yellow solid, 200 mg, 81% yield.

Workup

  1. customresulting in large granules of solid material which
  2. customThe chloroform was removed by pipette
  3. customthe remaining solid was triturated with dichloromethane

Sources & evidence

ORD record
ord-42558e90fbab450b94ba187d74f5f6a4
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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