2-Morpholinoethylamine → HCID 135817448, compound

HRID 991733Notes

Reaction equation

HRID 991733 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[OH:20])[N:10]([CH2:21][C:22](OCC)=[O:23])[N:9]=2)[CH:7]=1.[NH2:28][CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[OH:20])[N:10]([CH2:21][C:22]([NH:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:23])[N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 135914988HCID 135914988, compound

Product 1

HCID 135817448HCID 135817448, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 g of ethyl [3,5-bis(5-chloro-2-hydroxyphenyl)-[1,2,4]triazol-1-yl]acetate (Example 40) and 2.6 g of 4-(2-aminoethyl)morpholine are boiled under reflux for 18 h in 50 ml of ethanol. The mixture is cooled, poured onto water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated on a rotary evaporator. The residue is crystallized from isopropanol. After drying, 2-[3,5-bis(5-chloro-2-hydroxyphenyl)-[1,2,4]triazol-1-yl]-N-(2-morpholin-4-yl-ethyl)acetamide remains as colorless crystals of m.p. 224-226° C.

Workup

  1. temperatureThe mixture is cooled
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue is crystallized from isopropanol
  7. customAfter drying

Sources & evidence

ORD record
ord-fc24b0583c394c6ba6620d790d18d203
Source dataset
uspto-grants-2002_10
Patent number
US06465504B1

Reaction notes

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