Triethylamine → HCID 19040748, compound

HRID 1683903Notes

Reaction equation

HRID 1683903 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:18]=1[N+:26]([O-:28])=[O:27].C(N(CC)CC)C>O1CCCC1>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:17]3[C:18]([N+:26]([O-:28])=[O:27])=[CH:19][CH:20]=[CH:21][C:22]=3[N+:23]([O-:25])=[O:24])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118141-Chloro-2,6-dinitrobenzeneHCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 19040748HCID 19040748, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-3-(2-dimethylaminoethyl)indole and 1-chloro-2,6-dinitrobenzene were used. Triethylamine was used as base, tetrahydrofuran was used as solvent, and the reaction was stirred at room temperature for 1 hour. Chromatography afforded the title compound (57%) as a dark red solid: mp, 187.0°-188.0° C.; 13C NMR (DMSO-d6) δ139.9, 135.2, 134.0, 132.0, 131.8, 127.2, 123.8, 117.0, 115.4, 112.9, 112.0, 109.3, 59.9, 45.1, 23.0; HRMS calculated for C18H19N5O 369.1439, found 369.1428. Anal. calcd. for C18H19N5O: C, 58.53; H, 5.18; N, 18.96. Found: C, 58.45; H, 4.96; N, 18.63.

Sources & evidence

ORD record
ord-76e258133dca4b54ac560e16b50905c0
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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