Sodium Iodide → HCID 67264320, compound

HRID 1041052Notes

Reaction equation

HRID 1041052 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][NH:6][CH2:5][C:4]1=[O:19])[CH3:2].[CH2:20](Br)[CH3:21].[I-].[Na+].C(N(CC)C(C)C)(C)C.CN(C)C=O>>[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][N:6]([CH2:20][CH3:21])[CH2:5][C:4]1=[O:19])[CH3:2]

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 81531DiisopropylethylamineHCID 67263457HCID 67263457, compound

Product 1

HCID 67264320HCID 67264320, compound

Procedure

A mixture of 1-Ethyl-7-methoxy-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.42 g, 0.0016 mol), Ethyl bromide (0.244 mL, 0.00329 mol), Sodium iodide (0.0033 g, 0.000022 mol) and N,N-Diisopropylethylamine (1.14 mL, 0.00654 mol) in N,N-Dimethylformamide (4 mL, 0.05 mol) was stirred at room temperature for 22 hrs. The reaction was evaporated and the residue taken up in DCM/water, separated, washed, dried and evaporated to give 1,4-Diethyl-7-methoxy-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one the product as a red oil. (0.44 g, 95%). LCMS (m/e) 294 (M+1); 1H-NMR (DMSO, 400 MHz) δ 7.95 (s, 1H), 7.45 (s, 1H), 3.95 (s, 3H), 3.87-81 (q, 2H, J=6.82 Hz), 3.61 (s, 2H), 2.98 (s, 2H), 2.89 (s, 1H), 2.73 (s, 1H), 2.59-52 (q, 2H, J=7.07 Hz), 1.08-1.00 (quin, 6H, J=7.07 Hz).

Workup

  1. customThe reaction was evaporated
  2. customseparated
  3. washwashed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-46600d453a2d4b04bed685f2f75de3b4
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…