Methyl iodide → HCID 21851248, compound

HRID 617156Notes

Reaction equation

HRID 617156 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:7]=[C:6]2[N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28][N:29]2[C:38](=[O:39])[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([CH3:40])[CH:36]=3)[NH:31][C:30]2=[O:41])[CH2:23][CH2:22]1.[H-].[Na+].[CH3:44]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[N:7]=[C:6]2[N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28][N:29]2[C:38](=[O:39])[C:37]3[C:32](=[CH:33][CH:34]=[C:35]([CH3:40])[CH:36]=3)[N:31]([CH3:44])[C:30]2=[O:41])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 21851233HCID 21851233, compound

Product 1

HCID 21851248HCID 21851248, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 ml of dimethylformamide was suspended 350 mg (0.7 mmol) of Compound 29 obtained in Example 29, and 42 mg (1.05 mmol) of 60% sodium hydride and 0.1 ml (1.54 mmol) of methyl iodide were added to the suspension. The mixture was stirred at room temperature for one hour, and then a saturated aqueous solution of ammonium chloride was added thereto to stop the reaction. After extraction with ethyl acetate, the organic layer was washed and dried. The solvent was evaporated under reduced pressure, and the resulting crude crystals were washed with a solvent mixture of ethanol and ether to give 190 mg (yield: 48%) of Compound 30 as white crystals.

Workup

  1. additionwere added to the suspension
  2. customthe reaction
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. washthe resulting crude crystals were washed with a solvent mixture of ethanol and ether

Sources & evidence

ORD record
ord-04e742eb82854fc49ec00bedfae354c4
Source dataset
uspto-grants-1999_09
Patent number
US05948784

Reaction notes

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