Methyl iodide → HCID 22274384, compound

HRID 1064429

Reaction equation

HRID 1064429 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6](=[O:12])[C:5]2=[O:13].[H-].[Na+].[H][H].I[CH3:19]>CN(C=O)C.C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([CH3:19])[C:6](=[O:12])[C:5]2=[O:13]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 110093415,6-dichloro-1H-indole-2,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 22274384HCID 22274384, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5,6-dichloroisatin (0,15 g; 0.7 mmol) in anhydrous DMF (5 ml) was added sodium hydride (40 mg, 60% dispersion in mineral oil). When the evolution of hydrogen had ceased iodomethane (0.1 ml) was added and the mixture was stirred for 20 min. at ambient temperature. Water (15 ml) and glacial acetic acid (0.1 ml) were added and the product was filtered off, washed with water and dried to yield 5,6-dichloro-1-methylisatin (0.13 g, 81%). The following compounds were prepared analogously: 4,5-dichloro-1-methylisatin (2b) from 4,5-dichloroisatin, and 6,7-dichloro-1-methylisatin from 6,7-dichloroisatin.

Workup

  1. additionwas added
  2. filtrationthe product was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2dd4f14ba8ea4157b63e9421531775bc
Source dataset
uspto-grants-2005_11
Patent number
US06969729B2

Linked notes

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