Methyl iodide → HCID 9803683, compound

HRID 1600656Notes

Reaction equation

HRID 1600656 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH:22]=[N:21]3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[H-].[Na+].I[CH3:33]>CN(C=O)C>[CH3:33][N:24]1[C:23](=[O:27])[CH:22]=[N:21][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][N:13]2[CH2:12][CH2:11][N:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([F:2])([F:28])[F:29])[CH:5]=3)[CH2:15][CH2:14]2)[C:25]1=[O:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21830779HCID 21830779, compound

Product 1

HCID 9803683HCID 9803683, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound 1 (3.77 g; 0.009 mol is added dropwise to a 60% suspension of sodium hydride in paraffin oil (0.77 g; 0.019 mol) in DMF (50 ml), followed, after stirring for 2 hours at room temperature, by iodomethane (1.4 g; 0.01 mol). After leaving overnight at room temperature, the mixture is concentrated to dryness under vacuum and then the residue is taken up in water (100 ml) and extracted with ethyl ether (2×50 ml). The dried organic phases (Na2SO4) are concentrated to dryness under vacuum to give an oil which crystallizes slowly.

Workup

  1. customAfter leaving overnight at room temperature
  2. concentrationthe mixture is concentrated to dryness under vacuum
  3. extractionextracted with ethyl ether (2×50 ml)
  4. concentrationThe dried organic phases (Na2SO4) are concentrated to dryness under vacuum
  5. customto give an oil which
  6. customcrystallizes slowly

Sources & evidence

ORD record
ord-11a5ba2898b840d29e868f41c7feabbb
Source dataset
uspto-grants-1999_11
Patent number
US05977106

Reaction notes

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