Methyl iodide → HCID 21837489, compound

HRID 1739820Notes

Reaction equation

HRID 1739820 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24](=[O:29])[CH:23]=[C:22]3[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:9][C:10]([NH:12][CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16])=[S:11])=[CH:4][CH:3]=1.IC.[C:38](=O)([O-])[O-].[K+].[K+]>CC(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24](=[O:29])[CH:23]=[C:22]3[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:9][C:10]([S:11][CH3:38])=[N:12][CH2:13][CH:14]([O:15][CH3:16])[O:17][CH3:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21837460HCID 21837460, compound

Product 1

HCID 21837489HCID 21837489, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of intermediate (6-a) (15.3 g), iodomethane (2.27 ml) and potassium carbonate (5 g) in 2-propanone (50 ml) was stirred at room temperature for one night. The mixture was evaporated, the residue was taken up in DCM and washed with K2CO3 10%. The organic layer was dried (MgSO4), filtered off and evaporated, yielding 17.8 g (100%) of (±)-methyl N-[(4-chlorophenyl)(1,2-dihydro-2-oxo-4-phenyl-6-quinolinyl)-methyl]-N'-(2,2-dimethoxy-ethyl)carbamimidothioate (interm. 6-b), which was used without further purification.

Workup

  1. customThe mixture was evaporated
  2. washwashed with K2CO3 10%
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered off
  5. customevaporated

Sources & evidence

ORD record
ord-eb9c62962d8e4fac92412267b5507a83
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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