Dimethylformamide → HCID 67263639, compound

HRID 1687349Notes

Reaction equation

HRID 1687349 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8]([O:15][C:16]([N:18]1[CH2:24][C:23]2[CH:25]=[C:26]([O:32][CH3:33])[C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:22]=2[NH:21][C:20](=[O:34])[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.I[CH2:36][CH3:37]>CCCCCC>[CH2:8]([O:15][C:16]([N:18]1[CH2:24][C:23]2[CH:25]=[C:26]([O:32][CH3:33])[C:27]([N+:29]([O-:31])=[O:30])=[CH:28][C:22]=2[N:21]([CH2:36][CH3:37])[C:20](=[O:34])[CH2:19]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 67263771HCID 67263771, compound

Product 1

HCID 67263639HCID 67263639, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of Sodium hydride (0.135 g, 0.00338 mol) and N,N-Dimethylformamide (40 mL, 0.5 mol) was added at 5° C. 7-Methoxy-8-nitro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (1.00 g, 0.00269 mol) and stirred for 1 hour at room temperature. Iodoethane (0.286 mL, 0.00358 mol) was added and stirred for 3 hours. The solvent was evaporated and the residue taken up in water and ethyl acetate, separated, washed, dried and evaporated to a give a gum. Trituration with hexane gave 1-Ethyl-7-methoxy-8-nitro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-carboxylic acid benzyl ester as a red solid (1.01 g). (94%). Mp 55-56° C. LCMS (m/e) 400 (M+1); 1H-NMR (DMSO, 400 MHz) δ 8.02 (s, 1H), 7.58 (s, 1H), 7.50-7.30, (br, 5H), 5.15 (s, 2H), 4.56-4.48 (br, 2H), 3.94 (s, 3H), 3.91-3.84 (m, 4H), 1.05-1.01 (t, 3H, J=7.07 Hz).

Workup

  1. customThe solvent was evaporated
  2. customethyl acetate, separated
  3. washwashed
  4. customdried
  5. customevaporated to
  6. customa give a gum

Sources & evidence

ORD record
ord-22e0493f831d494d92bb37362eb42fac
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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