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Pyridine → 3-Benzothiazol-2-yl-3,5-dichloro-1,3-dihydroindol-2-one

HRID 2040420
Notes
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Reaction equation

HRID 2040420 reaction equation
N1C=CC=CC=1.S(Cl)(Cl)=O.[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1(O)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=2)[NH:22][C:21]1=[O:30].[Cl-:32].[NH4+]>ClCCl>[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[C:20]1([Cl:32])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=2)[NH:22][C:21]1=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 575177503-Benzothiazol-2-yl-5-chloro-3-hydroxy-1,3-dihydroindol-2-one

Product 1

HCID 575177513-Benzothiazol-2-yl-3,5-dichloro-1,3-dihydroindol-2-one

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

Pyridine (0.57 ml) and thionyl chloride (0.42 ml) were successively added to an ice-cooled solution of the intermediate from Step A (1.27 g, 4.0 mmol) in dichloromethane (40 ml). The reaction mixture was stirred at 0° C. for 1 h and then saturated ammonium chloride solution was added. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude intermediate was rapidly employed without further purification in the next step.

Workup

  1. dry with materialThe organic phase was dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude intermediate was rapidly employed without further purification in the next step

Sources & evidence

ORD record
ord-c9df193f59ab4383bc2423c97194d810
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580842B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes