Methyl iodide → HCID 19969448, compound

HRID 974808Notes

Reaction equation

HRID 974808 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:13]2[S:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[NH:9][C:8](=[O:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:23][N:9]1[C:8](=[O:18])[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:19])[F:20])[C:13]=2[S:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19969439HCID 19969439, compound

Product 1

HCID 19969448HCID 19969448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-trifluoromethyl-10,11-dihydrodibenzo[b,f][1,4]thiazepin-11-one (0.295 g, 1 mmol) in DMF (20 ml) was added sodium hydride (0.1 g of 60% dispersion in oil) and the resulting mixture stirred for 30 minutes, before methyl iodide (1 equivalent) was added. After stirring for 1 hour the mixture was evaporated and the residue separated between ethyl acetate and aqueous sodium bicarbonate. The organic fractions were dried (magnesium sulphate) and evaporated. Purification of the residue by chromatography on silica, eluting with ethyl acetate/petrol (1:1, v/v), followed by recrystallisation from cyclohexane gave the title compound as colourless needles (0.121 g, m.p. 139°-141°, Rf 0.41 [silica, ethyl acetate/petrol, 1:2, v/v]).

Workup

  1. additionwas added
  2. customwas evaporated
  3. customthe residue separated between ethyl acetate and aqueous sodium bicarbonate
  4. dry with materialThe organic fractions were dried (magnesium sulphate)
  5. customevaporated
  6. customPurification of the residue by chromatography on silica
  7. washeluting with ethyl acetate/petrol (1:1
  8. customv/v), followed by recrystallisation from cyclohexane

Sources & evidence

ORD record
ord-1780e4fa506d411788b55d4d20edffb5
Source dataset
uspto-grants-1997_03
Patent number
US05607929

Reaction notes

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