Water → HCID 21710150, compound

HRID 650902Notes

Reaction equation

HRID 650902 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]([CH3:14])[CH3:13])[C:6]2=[O:11].C1C(=O)N([Cl:22])C(=O)C1.O>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:22])=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]([CH3:14])[CH3:13])[C:6]2=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 21710156HCID 21710156, compound

Product 1

HCID 21710150HCID 21710150, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.8 grams (0.015 mole) of 4-amino-2-(1-methylethyl)isoindolin-1-one and 2.0 grams (0.015 mole) of NCS in 80 mL of DMF was stirred at 25° C. for about 18 hours. The reaction mixture was then poured into water, and the mixture was extracted repeatedly with diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel using mixtures of EtOAc and methylene chloride as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding about 1.0 gram of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionthe mixture was extracted repeatedly with diethyl ether
  2. dry with materialThe combined extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure to a residue
  5. customThe residue was purified by column chromatography on silica gel using mixtures of EtOAc and methylene chloride as eluants
  6. additionThe fractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bfa92bf117a42339587e1f7787b5238
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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