Diethyl Ether → HCID 21467113, compound

HRID 53505Notes

Reaction equation

HRID 53505 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[NH:11][C:10]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22](=O)([O-])[O-].[Cs+].[Cs+].IC.C(OCC)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[N:11]([CH3:22])[C:10]1=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 146664143-t-butyloxycarbonylamino-3,4-dihydro-1H-1-benzazepine-2,5-dione

Product 1

HCID 21467113HCID 21467113, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-t-butyloxycarbonylamino-3,4-dihydro-1H-1-benzazepine-2,5-dione (500 mg, 1.72 mmol) in 25 ml anhydrous DMF was-added cesium carbonate (562 mg) followed by iodomethane (215 μl). The reaction was stirred for one hour, diluted with ethyl acetate and then washed with water. The organic phase was separated, washed with brine, dried (MgSO4) and concentrated to give a yellow solid. Tritiation with diethyl ether gave 3-t-butyloxycarbonylamino-1-methyl-3,4-dihydro-1H-1-benzazepine-2,5-dione as a colourless solid. 1H NMR (250 MHz, CDH3) δ 7.64-7.50 (M, 2H) 7.38-7.24 (t, 1H) 7.20-7.60 (d, 1H,) 5.78-5.66 (br d, 1H,) 4.98-4.82 (M, 1H) 3.40 (s, 3H) 3.36-3.20 (dd, 2H) 2.98-2.80 (dd, 2H).

Workup

  1. washwashed with water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a yellow solid

Sources & evidence

ORD record
ord-065c284e4ef24a0192ffdf3b5dbef502
Source dataset
uspto-grants-1997_04
Patent number
US05620972

Reaction notes

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