Hydrochloric Acid → 5-Chloro-3-(5-bromo-2-furanoyl)-2-oxindole-1-carboxamide

HRID 486154Notes

Reaction equation

HRID 486154 reaction equation
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]([NH2:22])=[O:21])[C:15](=[O:23])[CH2:14]2.BrC1OC(C(Cl)=O)=CC=1.Cl>S(Cl)(Cl)=O.CN(C1C=CN=CC=1)C.CN(C)C=O>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:20]([NH2:22])=[O:21])[C:15](=[O:23])[CH:14]2[C:7]([C:5]1[O:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 685115-Bromo-2-furanecarboxylic acidHCID 27570115-Bromofuran-2-carbonyl chlorideHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide

Product 1

HCID 867450435-Chloro-3-(5-bromo-2-furanoyl)-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

Using the procedure of Example 32, 1.91 g (10.0 mmoles) of commercially available 5-bromo-2-furancarboxylic acid was dissolved in 10 ml of thionyl chloride and heated to reflux under nitrogen for 1 hour and the acid chloride product was recovered. A 40 ml N,N-dimethylformamide solution of 1.75 g (8.3 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 3.05 g (25 mmoles) of 4-(N,N-dimethylamino)pyridine was reacted with 2.09 g (10 mmoles) of 5-bromo-2-furan carbonyl chloride in 10 ml of N,N-dimethylformamide. After a reaction time of about 45 minutes, the mixture was acidified by pouring into 250 ml of 1N HCl. The product was recrystallized from acetic acid, washed with acetic acid, then hexane and dried overnight in vacuo at room temperature. The resulting product then was dried over refluxing isopropanol under high vacuum to yield 1.37 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 1 hour
  3. customthe acid chloride product was recovered
  4. customAfter a reaction time of about 45 minutes
  5. customThe product was recrystallized from acetic acid
  6. washwashed with acetic acid
  7. dry with materialhexane and dried overnight in vacuo at room temperature
  8. customThe resulting product then was dried
  9. temperatureover refluxing isopropanol under high vacuum

Sources & evidence

ORD record
ord-032d7070491d46f4be398d7171c3b0bf
Source dataset
uspto-grants-1994_03
Patent number
US05290802

Reaction notes

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