Methyl iodide → 1-(10,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone

HRID 1826672Notes

Reaction equation

HRID 1826672 reaction equation
[CH:1]1[C:11]2[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[C:8]3[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].I[CH3:25]>CN(C)C=O>[CH3:25][N:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 221352391-(10,11-Dihydro-5H-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone

Product 1

HCID 221352361-(10,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(10,11-Dihydro-5H-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone of Step A (3.12 g) was added to dry N,N-dimethylformamide (50 mL) containing sodium hydride (60% dispersion in oil, 0.60 g, washed with hexane). After a short while iodomethane was added (2.0 g) and the mixture stirred overnight at room temperature, quenched with ice and diluted with brine. The precipitate was collected and redissolved in dichloromethane. The solution was dried over anhydrous sodium sulfate and filtered through a short column of Magnesol® which was eluted with several additional volumes of dichloromethane. The total effluent was evaporated to dryness and the residue crystallized from hexane to provide the title compound as colorless crystals (1.23 g), m.p. 104–106° C.

Workup

  1. customquenched with ice
  2. additiondiluted with brine
  3. customThe precipitate was collected
  4. dissolutionredissolved in dichloromethane
  5. dry with materialThe solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered through a short column of Magnesol® which
  7. washwas eluted with several additional volumes of dichloromethane
  8. customThe total effluent was evaporated to dryness
  9. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-56a5d9285ca8439ca6f34ab0c70c6ede
Source dataset
uspto-grants-2006_05
Patent number
US07053083B2

Reaction notes

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