Triethylamine → HCID 3573319, compound

HRID 480023Notes

Reaction equation

HRID 480023 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.C(N(CC)CC)C>C(Cl)Cl>[N:17]1([CH2:16][CH2:15][CH2:14][NH:13][C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 3573319HCID 3573319, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-nitrobenzoyl chloride (18.5 g, 0.1 mol) in DCM (200 ml) was added dropwise to a stirred solution of 1-(3-aminopropyl)imidazole (14.0 g, 0.112 mol) and triethylamine (15 ml, 0.107 mol) in DCM (200 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour, and the solid which had separated out was collected by filtration and washed with water (100 ml) and acetone (100 ml) to give the product (21.6 g, 79%). NMR: 1.9-2.0 (m, 2H), 3.2-3.3 (m, 2H), 4.0 (t, 2H), 6.85 (s, 1H), 7.2 (s, 1H), 7.65 (s, 1H), 8.05 (d, 2H), 8.3 (d, 2H), 8.8 (br s, 1H).

Workup

  1. customthe solid which had separated out
  2. filtrationwas collected by filtration
  3. washwashed with water (100 ml) and acetone (100 ml)

Sources & evidence

ORD record
ord-baa65646b1494b059601e3c0ba9e83e2
Source dataset
uspto-grants-2003_11
Patent number
US06649608B2

Reaction notes

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