Ethanolamine → 1,2-Bis(4-chlorophenyl)-2-[(2-hydroxyethyl)amino]ethan-1-one--hydrogen chloride (1/1)

HRID 1381514

Reaktionsgleichung

Reaktionsgleichung von HRID 1381514
[Cl:1]C1(Cl)C=CC(C(C(C2C=CC=CC=2)O)=O)=CC1.[CH2:19]([CH2:21][NH2:22])[OH:20].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:32]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=O)=[O:31])=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[ClH:1].[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([CH:32]([NH:22][CH2:21][CH2:19][OH:20])[C:30]([C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=2)=[O:31])=[CH:35][CH:36]=1

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 189461,2-Ethanedione, 1,2-bis(4-chlorophenyl)-HCID 70383126HCID 70383126, Verbindung

Produkt 1

HCID 143911771,2-Bis(4-chlorophenyl)-2-[(2-hydroxyethyl)amino]ethan-1-one--hydrogen chloride (1/1)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

In a closed system equipped with a Dean-Stark trap, a stirred solution of 4,4-dichlorobenzoin (10.0 g, 0.0357 mole), ethanolamine (2.35 g, 0.0385 mole), and a catalytic amount of p-toluenesulfonic aid in 250 ml toluene was heated at reflux temperature for 4 hours and the azeotroped water was collected in the Dean-Stark trap. After cooling, the toluene solution was washed with water, dried over magnesium sulfate and concentrated to an oil. The oil was dissolved in ether, treated with excess ethereal hydrogen chloride and the salt collected under nitrogen. Upon trying to recrystallize the salt from 350 ml of isopropyl ether (necessary for complete solution), 500 ml isopropyl ether, a yellow solid was obtained from this solution which was identified as 4,4'-dichlorobenzil. The filtrate was concentrated to 50 ml and isopropyl ether added to the hot solution until a faint turbidity was obtained. On standing overnight, a white solid was obtained, m.p. 177°-182° C. Recrystallization of the white solid from methanol-isopropyl ether and from acetonitrile-methanol yielded only semisolid salts. These were triturated with methyl ethyl ketone and dried to give 2.04 g total, m.p. 188°-193° C. This material gave a satisfactory elemental analysis for the title compound.

Aufarbeitung

  1. customIn a closed system equipped with a Dean-Stark trap
  2. temperatureat reflux temperature for 4 hours
  3. customthe azeotroped water was collected in the Dean-Stark trap
  4. temperatureAfter cooling
  5. washthe toluene solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to an oil
  8. dissolutionThe oil was dissolved in ether
  9. additiontreated with excess ethereal hydrogen chloride
  10. customthe salt collected under nitrogen
  11. customto recrystallize the salt from 350 ml of isopropyl ether (necessary for complete solution), 500 ml isopropyl ether
  12. customa yellow solid was obtained from this solution which
  13. concentrationThe filtrate was concentrated to 50 ml and isopropyl ether
  14. additionadded to the hot solution until a faint turbidity
  15. customwas obtained
  16. customa white solid was obtained
  17. customRecrystallization of the white solid from methanol-isopropyl ether
  18. customfrom acetonitrile-methanol yielded only semisolid salts
  19. customThese were triturated with methyl ethyl ketone
  20. customdried
  21. customto give 2.04 g total

Quellen und Nachweise

ORD-Eintrag
ord-584452cd798c4d82b078936f66e75e01
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803200

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