Triethylamine → HCID 86048447, compound

HRID 1865805Notes

Reaction equation

HRID 1865805 reaction equation
Cl[C:2]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[O:5].CC[N:26]([CH2:29][CH3:30])CC.N1CC1>CCOC(C)=O>[N:26]1([C:2]2[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[CH:14][C:3]=2[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[O:5])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9033AziridineHCID 86048448HCID 86048448, compound

Product 1

HCID 86048447HCID 86048447, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-chloro-N-(6-hydroxyhexyl)-3,5-dinitrobenzamide (16) [for preparation see Example 14 below] (118 mg, 0.34 mmol) and Et3N (200 mg) in EtOAc (200 mL) was treated with aziridine (100 mg) at room temperature for 3 h. The mixture was diluted with EtOAc and washed three times with water, after dry, concentrated under reduced pressure until about 20 mL, the yellow solid was collected and gave 101 mg product (84%); 1H NMR [(CD3)2SO] δ 8.74 (d, J=2.8 Hz, 1 H), 8.63 (m, 1 H), 8.29 (d, J=2.8 Hz, 1 H), 4.31 (m, 1 H), 3.39 (m, 2 H), 3.25 (m, 2 H), 2.37 (s, 4 H), 1.56 (m, 2 H), 1.43 (m, 2 H), 1.33 (m, 4 H). Anal. (C15H20N4O6) C, H, N.

Workup

  1. washwashed three times with water
  2. customafter dry
  3. concentrationconcentrated under reduced pressure until about 20 mL
  4. customthe yellow solid was collected

Sources & evidence

ORD record
ord-79ff7128d62847659b01a55b63d70328
Source dataset
uspto-grants-2009_12
Patent number
US07629332B2

Reaction notes

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