Methyl iodide → HCID 20392228, compound

HRID 1863186Notes

Reaction equation

HRID 1863186 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[O:13])[C:4]2=[CH:14][S:15][CH:16]=[C:3]12.[H-].[Na+].[CH3:19]I>CN(C)C=O>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH3:19])[C:5](=[O:13])[C:4]2=[CH:14][S:15][CH:16]=[C:3]12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 20392228HCID 20392228, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.8 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 620 mg. of 50% sodium hydride in mineral oil in 30 ml. of dry dimethylformamide is stirred for 11/4 hours. A 2.1 g. portion of methyl iodide is added and the mixture is stirred overnight. The mixture is poured onto ice water and the solid is collected and dried. The solid changes to a glass which is dissolved in methylene chloride, washed with water, filtered and concentrated to dryness. The crude oily solid is triturated in hexane and ether. The ether hexane mixture is concentrated to a yellow gum, dissolved in 15 ml. of 30% methylene chloride in hexane and chromatographed on an alumina column, eluting with the same solvent. Four 200 ml. fractions are collected. The solvent is changed to methylene chloride:hexane (50:50) for fractions 5-8 (200 ml.). The solvent is changed to 100% methylene chloride for fractions 8-11 (200 ml.). The solvent is changed to 20% ethyl acetate in benzene for fractions 12-19 (200 ml.). Fractions 11-19 are combined and concentrated to a yellow oil which crystallizes with trituration in hexane, giving the desired product, mp. 101°-102° C.

Workup

  1. additionA mixture of 2.8 g
  2. additionThe mixture is poured onto ice water
  3. customthe solid is collected
  4. customdried
  5. dissolutionThe solid changes to a glass which is dissolved in methylene chloride
  6. washwashed with water
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude oily solid is triturated in hexane
  10. concentrationThe ether hexane mixture is concentrated to a yellow gum
  11. dissolutiondissolved in 15 ml
  12. customof 30% methylene chloride in hexane and chromatographed on an alumina column
  13. washeluting with the same solvent
  14. customfractions are collected
  15. concentrationconcentrated to a yellow oil which
  16. customcrystallizes with trituration in hexane

Sources & evidence

ORD record
ord-e4d9ce48d6d6442a85e8652ecce26759
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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