Methyl iodide → HCID 69020511, compound

HRID 860781Notes

Reaction equation

HRID 860781 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:30]=[CH:29][C:7]([C:8]([C:10]2[CH:11]=[CH:12][C:13]3[NH:19][C:18](=[O:20])[CH2:17][N:16]=[C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[C:14]=3[CH:28]=2)=[O:9])=[CH:6][CH:5]=1.I[CH3:32]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:19]([CH3:32])[C:18](=[O:20])[CH2:17][N:16]=[C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[C:14]=3[CH:28]=2)=[O:9])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69018742HCID 69018742, compound

Product 1

HCID 69020511HCID 69020511, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH 80% in oil (0.0366 mol) was added at 10° C. under N2 flow to a mixture of intermediate (6) (0.0244 mol) in N,N-dimethylformamide (100 ml). The mixture was brought to room temperature and then stirred for 30 min. and iodomethane (0.0293 mol) was added. The mixture was stirred for 3 hours, hydrolyzed, filtered, washed with water and taken up in DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (9.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 4.5 g (43%) of 7-(4-chlorobenzoyl)-5-(3-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (intermediate 7), mp. 176° C.

Workup

  1. customwas brought to room temperature
  2. stirringThe mixture was stirred for 3 hours
  3. filtrationhydrolyzed, filtered
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated till dryness
  9. customThe residue (9.1 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15–40 μm)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from 2-propanone
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-9f9decba967d4f4784253316a47f8ae5
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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