Cyanogen Bromide → 4-(2-Aminobenzo[d]thiazole-4-sulfonamido)benzoic acid

HRID 2202412Notes

Reaction equation

HRID 2202412 reaction equation
[NH2:1][C:2]1[C:7]([SH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)(=[O:11])=[O:10].[N:22]#[C:23]Br>C1COCC1>[NH2:22][C:23]1[S:8][C:7]2[C:2](=[C:3]([S:9]([NH:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)(=[O:10])=[O:11])[CH:4]=[CH:5][CH:6]=2)[N:1]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 904190184-(2-Amino-3-mercaptophenylsulfonamido)benzoic acid

Product 1

HCID 904190924-(2-Aminobenzo[d]thiazole-4-sulfonamido)benzoic acidYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2-amino-3-mercaptophenylsulfonamido)benzoic acid (671 mg, 2.07 mmol) in THF (15 mL) was added cyanic bromide (439.1 mg, 4.14 mmol) at r.t. The reaction mixture was stirred at 80° C. for 8 h. The resulting mixture was then cooled, and partitioned between water and EtOAc. The organic phase was washed with brine, dried over anhy. Na2SO4 and concentrated in vacuo to afford the title compound (730 mg). LC-MS: m/z 348.7 (M+H)+

Workup

  1. temperatureThe resulting mixture was then cooled
  2. custompartitioned between water and EtOAc
  3. washThe organic phase was washed with brine
  4. customdried over anhy
  5. concentrationNa2SO4 and concentrated in vacuo

Sources & evidence

ORD record
ord-31d9be98837f44148bd169a43e98d0c1
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

Loading…