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

HRID 514876Notes

Reaction equation

HRID 514876 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-415e914287084f788a0b7290dcdf5e21
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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