Water → HCID 11687526, compound

HRID 1867572Notes

Reaction equation

HRID 1867572 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:15])[N:6]2[CH2:11][C:12]([NH2:14])=[O:13].C1C(=O)N([Cl:23])C(=O)C1.O>OS(O)(=O)=O>[Cl:1][C:2]1[C:10]([Cl:23])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:15])[N:6]2[CH2:11][C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 115214431H-Indole-1-acetamide, 4-chloro-2,3-dihydro-2-oxo-

Product 1

HCID 11687526HCID 11687526, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-(4-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 7 (0.205 g, 0.9 mmol) is dissolved in 90% H2SO4 (1 ml) at room temperature, and NCS (0.12 g, 0.9 mmol) is slowly added with stirring. After 2 hours, the mixture is poured into cold water. The precipitate is collected, washed several times with water and then with Et2O. The crude reaction mixture is purified by column chromatography on silicagel (CH2Cl2/EtOH/NH4OH: 94.5/5/0.5 (v/v)) to afford the 2-(4,5-dichloro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 10 as a white solid.

Workup

  1. customThe precipitate is collected
  2. washwashed several times with water
  3. customThe crude reaction mixture
  4. customis purified by column chromatography on silicagel (CH2Cl2/EtOH/NH4OH: 94.5/5/0.5 (v/v))

Sources & evidence

ORD record
ord-4c26d7cdc25e4a48a31d442bfbb8e5d0
Source dataset
uspto-grants-2009_12
Patent number
US07632856B2

Reaction notes

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