Methyl iodide → HCID 19383079, compound

HRID 2399681Notes

Reaction equation

HRID 2399681 reaction equation
[CH3:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5](=[O:13])[CH:4]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[N:3]=1.[H-].[Na+].I[CH3:28]>CN(C)C=O>[CH3:28][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:2]([CH3:1])=[N:3][CH:4]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C:5]1=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135744107HCID 135744107, compound

Product 1

HCID 19383079HCID 19383079, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-dihydro-5-methyl-3(R,S)[-(benzyloxycarbonyl )-amino]-2H- 1,4-benzodiazepin-2-one (2 g, 6.2 mmol) in dimethylformamide (20 ml), under an atmosphere of nitrogen, was treated with sodium hydride (0.26 g of a 57% dispersion in mineral oil, 6.2 mmol) in one portion, at -10° C. After 30 min, iodomethane (0.39 ml, 6.2 mmol) was added and the resulting mixture stirred at room temperature for 3 h. The solvent was then evaporated and the crude residue partitioned between water (20 ml) and dichloromethane (3×20 ml). The combined organic phase was washed with brine (20 ml), dried (MgSO4) and evaporated. The residue was triturated with ether to afford the title compound (1.05 g, 50%) as a colourless solid. 1H NMR (360 MHz, CDCl3) δ 2.52 (3H, s), 3.42 (3H, s), 5.0-5.25 (3H, m), 6.65 (1H, d, J=8 Hz), 7.2-7.7 (9H, m).

Workup

  1. customat -10° C
  2. customThe solvent was then evaporated
  3. customthe crude residue partitioned between water (20 ml) and dichloromethane (3×20 ml)
  4. washThe combined organic phase was washed with brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-f0c2af8fef9c44579c471ba3728b08d1
Source dataset
uspto-grants-1995_09
Patent number
US05451582

Reaction notes

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