Chloroform → HCID 18976182, compound

HRID 2393588Notes

Reaction equation

HRID 2393588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].Cl.[NH2:13][CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:15]1=[O:28].C(=O)([O-])O.[Na+].C(Cl)(Cl)Cl>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:13][CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:15]1=[O:28])=[O:6]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 516892Sodium BicarbonateHCID 18976150HCID 18976150, compound

Product 1

HCID 18976182HCID 18976182, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere and ice cooling, a solution of 2.80 g of 3,4-dichlorobenzoyl chloride in 20 ml of methylene chloride was added dropwise to a mixture of 2.84 g of 3-amino-1-pentyl-2,3-dihydro-1H-indol-2-one hydrochloride, 2.24 g of sodium hydrogen carbonate, 30 ml of chloroform and 30 ml of water. The reaction mixture was stirred under ice cooling for 30 minutes and then at room temperature for 30 minutes, diluted with water and extracted with chloroform. After the chloroform layer was washed and dried, the solvent was removed by evaporation. The residue was recrystallized from ethyl acetate-hexane to afford 4.06 g of 3,4-dichloro-N-(2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl)benzamide as colorless crystals. Melting point: 125° to 126° C., IR (Nujol) (cm-1): 3280, 1725, 1635, 1610, MS (m/z): 390 (M+), 374, 372, 217 (base).

Workup

  1. waitat room temperature for 30 minutes
  2. extractionextracted with chloroform
  3. washAfter the chloroform layer was washed
  4. customdried
  5. customthe solvent was removed by evaporation
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-710f6c35a4c448fd8d175fa2d6d4ae75
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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