1,2,3-Benzothiadiazole-7-carboxylic acid, methyl ester → Methyl 3-amino-2-mercaptobenzoate

HRID 2301020Notes

Reaction equation

HRID 2301020 reaction equation
[S:1]1[C:5]2[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=N1>O1CCOCC1.[Pd]>[NH2:3][C:4]1[C:5]([SH:1])=[C:6]([CH:7]=[CH:8][CH:9]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 1

HCID 1794011,2,3-Benzothiadiazole-7-carboxylic acid, methyl ester

Product 1

HCID 18377608Methyl 3-amino-2-mercaptobenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1 g of methyl benzo-1,2,3-thiadiazole-7-carboxylate in 40 ml of dioxane is hydrogenated over 0.5 g of palladium-on-charcoal (5%) at 160° C under an initial pressure of 150 bar. After the starting substance has reacted completely, the catalyst is filtered off and rinsed with dioxane, the filtrate is evaporated, avoiding contact with air, and the residue is purified over silica gel (hexanelethyl acetate (6:4)). The title compound of melting point 174-175° C. is obtained by this procedure.

Workup

  1. customAfter the starting substance has reacted completely
  2. filtrationthe catalyst is filtered off
  3. washrinsed with dioxane
  4. customthe filtrate is evaporated
  5. customthe residue is purified over silica gel (hexanelethyl acetate (6:4))

Sources & evidence

ORD record
ord-f1f4ca4002314c9893e8e7d391897d28
Source dataset
uspto-grants-2002_12
Patent number
US06498265B2

Reaction notes

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