Water → 7-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acid

HRID 79032Notes

Reaction equation

HRID 79032 reaction equation
C([O:5][C:6]([C:8]1[CH:16]=[CH:15][C:11]2[CH:12]=[N:13][S:14][C:10]=2[C:9]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[F:25])=[O:7])(C)(C)C.O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:19]1[CH:20]=[C:21]([I:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:9]1[C:10]2[S:14][N:13]=[CH:12][C:11]=2[CH:15]=[CH:16][C:8]=1[C:6]([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 575215037-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acid tert-butyl ester

Product 1

HCID 575215047-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(2-fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acid tert-butyl ester (710 mg, 1.51 mmol) in DCM (5 mL) were added water (0.15 mL) and TFA (5 mL). The reaction mixture was stirred at room temperature for 1 hour before being concentrated in vacuo. The resultant residue was azeotroped with toluene to give the title compound as a yellow solid (571 mg, 91%). LCMS (method B): RT=3.95 min, [M+H]+=415.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe resultant residue was azeotroped with toluene

Sources & evidence

ORD record
ord-9a5cc4f4a3ca42128d2de103596395ac
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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