Thionyl Chloride → HCID 68690559, compound

HRID 12615Notes

Reaction equation

HRID 12615 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:15][C:16]([OH:18])=[O:17])=[CH:9][NH:10]2.[C:19](=O)([O-])O.[Na+]>CO>[CH3:19][CH:15]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[Br:5])[NH:10][CH:9]=1)[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 13499084(4-Bromo-1H-indol-3-yl)acetic acid

Product 1

HCID 68690559HCID 68690559, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methanol (10 mL), thionyl chloride (0.76 mL) was added dropwise at −15 to −10° C., followed by stirring for 30 minutes. To the mixture, (4-bromo-1H-indol-3-yl)acetic acid (Chemical and Pharmaceutical Bulletin, 33(9), 3696-3708 (1985), 1.32 g) was added, followed by stifling at room temperature for 2 hours. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried and then concentrated. The residue was washed with diisopropyl ether/n-hexane (1:2) to obtain the titled compound having the following physical properties (1.26 g).

Workup

  1. waitby stifling at room temperature for 2 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed in turn with water and saturated saline
  4. customdried
  5. concentrationconcentrated
  6. washThe residue was washed with diisopropyl ether/n-hexane (1:2)

Sources & evidence

ORD record
ord-670c665077724bca8cf125a62ee6991a
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Reaction notes

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