Sodium Hydroxide → 6-Amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acid

HRID 2039607Notes

Reaction equation

HRID 2039607 reaction equation
C[O:2][C:3]([C:5]1[C:6]([NH2:15])=[C:7]([Cl:14])[C:8]2[C:9]([CH:13]=1)=[N:10][S:11][N:12]=2)=[O:4].[OH-].[Na+]>O1CCOCC1.CO>[NH2:15][C:6]1[C:5]([C:3]([OH:4])=[O:2])=[CH:13][C:9]2=[N:10][S:11][N:12]=[C:8]2[C:7]=1[Cl:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 578559926-Amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acid methyl ester

Product 1

HCID 578559746-Amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acidYield 84.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.37 g (1.50 mmol) of 6-amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acid methyl ester in 7.32 mL of dioxane and 0.92 mL of MeOH, is added 2.25 mL (2.25 mmol) of an aqueous solution of NaOH 1 N. The mixture is stirred at ambient temperature during 2 hours and then the solvents were evaporated. The residue is suspended in H2O and the mixture is acidified to pH 2-3 with an aqueous 1 N HCl solution. The reddish-violet precipitate obtained is filtrated and washed with a minimum of H2O. 291 mg (1.27 mmol) of the expected product can be isolated. The aqueous phase is extracted with EtOAc (2 times) and then the organic layer is washed once with brine, dried on Na2SO4, filtrated and concentrated under reduced pressure. 10 mg (43.54 ?mol) of the acid is obtained more giving a total amount of 301 mg (1.31 mmol, 87%) of a dark violet solid. LC/MS: 230/232 (M+1)+.

Workup

  1. customthe solvents were evaporated
  2. customThe reddish-violet precipitate obtained
  3. filtrationis filtrated
  4. washwashed with a minimum of H2O

Sources & evidence

ORD record
ord-ea52c945da6d427ab5d6ce21bdcdbde8
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

Loading…