Triethylamine → [2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid anthracen-9-ylmethyl ester

HRID 341567

Reaktionsgleichung

Reaktionsgleichung von HRID 341567
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.Cl[C:18](OC1C=CC([N+]([O-])=O)=CC=1)=[O:19].C(N(CC)CC)C.[NH2:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][OH:43]>C(Cl)Cl.[Au]>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][O:16][C:18](=[O:19])[NH:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][OH:43])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 13578DiglycolamineHCID 738489-AnthracenemethanolHCID 821294-Nitrophenyl chloroformate

Produkt 1

HCID 10315131[2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid anthracen-9-ylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23985GoldKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirring slurry of 9-anthracenemethanol (10 g, 48 mmol) and 4-nitrophenyl chloroformate (13.6 g, 67.5 mmol) in 200 ml CH2Cl2 was added triethylamine (6.7 ml, 0.19 mol). The resulting gold colored solution was allowed to stir 16 hrs at room temperature. At this point, 2-(2-aminoethoxy)ethanol (14.4 ml, 0.144 mol) was added and stirring continued for another 24 hours. The CH2Cl2 reaction mixture was then washed with a 2% sodium hydroxide (w/w) solution until no p-nitrophenol was observed in the organic layer. The dichloromethane was dried with sodium sulfate, filtered, and evaporated under reduced pressure.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for another 24 hours
  3. washwas then washed with a 2% sodium hydroxide (w/w) solution until no p-nitrophenol
  4. dry with materialThe dichloromethane was dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3d1c8c674c9949dca91664f1b2560a93
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895787B2

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