Acetyl chloride → HCID 69659259, compound

HRID 1828995Notes

Reaction equation

HRID 1828995 reaction equation
N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1.[CH:21]([N:24](CC)C(C)C)(C)[CH3:22].C(Cl)(=[O:32])C>C1COCC1>[O:20]=[C:12]1[C:11](=[C:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([CH2:22][C:21]([NH2:24])=[O:32])[CH:10]=3)[CH2:6][O:7]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 69659259HCID 69659259, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(6-Amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (50.0 mg, 0.189 mmol) and N,N-diisopropylethylamine (98.8 μL, 0.567 mmol) in 2.0 mL THF was added acetyl chloride (13.4 μL, 0.189 mmol). After stirring at room temperature for 1 h, the slurry was partitioned between NaHCO3 solution and EtOAc (warmed to dissolve solid). The organic phase was washed with H2O, 4% aqueous HCl solution, H2O, saturated NaHCO3, brine and dried with Na2SO4. After concentrating in vacuo the residue was triturated with EtOAc to give the title compound (47.4 mg, 82%) as a yellow solid.

Workup

  1. customthe slurry was partitioned between NaHCO3 solution and EtOAc (warmed to dissolve solid)
  2. washThe organic phase was washed with H2O, 4% aqueous HCl solution, H2O, saturated NaHCO3, brine
  3. dry with materialdried with Na2SO4
  4. concentrationAfter concentrating in vacuo the residue
  5. customwas triturated with EtOAc

Sources & evidence

ORD record
ord-f6ebe81e8af34be68e6c802ba13b0be3
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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