Hydrogen iodide → 3-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1,3-dihydro-2H-indol-2-one

HRID 1965225Notes

Reaction equation

HRID 1965225 reaction equation
O[C:2]1([C:12]2[C:21]([OH:22])=[CH:20][C:15]3[N:16]=[C:17]([CH3:19])[S:18][C:14]=3[CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].I>O.C(OCC)(=O)C>[OH:22][C:21]1[C:12]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][C:3]2=[O:11])=[CH:13][C:14]2[S:18][C:17]([CH3:19])=[N:16][C:15]=2[CH:20]=1

Participants

5

Reactant 2

HCID 24841Hydrogen iodideHCID 673568823-hydroxy-3-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 685981443-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1,3-dihydro-2H-indol-2-oneYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-hydroxy-3-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1,3-dihydro-2H-indol-2-one (4.81 g, 15.4 mmol) and 48% aqueous hydroiodic acid (25 mL) was heated at reflux for 1 h. The reaction mixture was allowed to cool to ambient temperature and was diluted with water (50 mL) and ethyl acetate (50 mL). The mixture was briefly sonicated, causing a precipitate to be deposited. The solid was collected by filtration, washed with water (20 mL) and dried in vacuo to afford 3-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1,3-dihydro-2H-indol-2-one (4.52 g, 99%) as a pale yellow solid: MS (ES+) m/z 297.2 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customThe mixture was briefly sonicated
  4. filtrationThe solid was collected by filtration
  5. washwashed with water (20 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-852a8f541d0e4ae2b7cef67bcc581758
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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