Triethylamine → HCID 15389234, compound

HRID 1976845Notes

Reaction equation

HRID 1976845 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[C:21]2[C:12]([NH:13][C:14]3[C:15]([N+:25]([O-:27])=[O:26])=[CH:16][CH:17]=[C:18](Cl)[C:19]=3[C:20]2=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][CH2:32][NH2:33])[CH3:29].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.CS(C)=O.O>[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][CH2:32][NH:33][C:18]1[C:19]2[C:20](=[O:23])[C:21]3[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:22]=3)[NH:13][C:14]=2[C:15]([N+:25]([O-:27])=[O:26])=[CH:16][CH:17]=1)[CH3:29]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 60993N,N-DiethylethylenediamineHCID 135883221-Chloro-4-nitro-7-(phenylmethoxy)-9(10H)-acridinone

Product 1

HCID 15389234HCID 15389234, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7-benzyloxy-1-chloro-4-nitroacridin-9(10H)-one (IV-P) (9.52 g, 25 mmol), 2-diethylaminoethylamine (4.3 ml, 30 mmol) and triethylamine (3.5 ml, 25 mmol) in dimethylformamide or dimethyl sulphoxide (150 ml) was stirred and heated at 60° C. for 1 hour. Next water (500 ml) and a concentrated solution of sodium carbonate (40 ml) were added and the precipitate was filtered, washed with water and dried to give 10.8 g (94%) of crude product. Crystallisation from dimethylformamide (100 ml) gave analytically pure product, yield 10 g (87%).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-34679dab14ee4e07b650699c9ae7e889
Source dataset
uspto-grants-2001_05
Patent number
US06229015B1

Reaction notes

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