Hydrazine hydrate (1:1) → 4-(2-Amino-3-mercaptophenylsulfonamido)benzoic acid

HRID 2202411Notes

Reaction equation

HRID 2202411 reaction equation
[S:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([S:10]([NH:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)(=[O:12])=[O:11])=[C:4]2[N:3]=C1.O.NN>CCO>[NH2:3][C:4]1[C:5]([SH:1])=[CH:6][CH:7]=[CH:8][C:9]=1[S:10]([NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 904189724-(Benzo[d]thiazole-4-sulfonamido)benzoic acid

Product 1

HCID 904190184-(2-Amino-3-mercaptophenylsulfonamido)benzoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 4-(benzo[d]thiazole-4-sulfonamido)benzoic acid (500 mg, 1.5 mmol) in 6 mL of EtOH was added hydrazine hydrate (479 mg, 15 mmol) at r.t. The reaction mixture was then stirred at 130° C. in microwave for 1.5 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 (449.0 mg). LC-MS: m/z 323.4 (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-f758fce5219f408dacb7d617f7fdfb27
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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