Toluene → 2-chloro-N-(2-hydroxyethyl)-N-methylbenzeneacetamide

HRID 358206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358206
Cl[O:2][C:3](=O)[CH2:4]C1C=CC=CC=1.S(Cl)([Cl:14])=O.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:23][NH:24][CH:25]([OH:27])C>CN(C)C=O.C(Cl)Cl>[Cl:14][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:22][C:25]([N:24]([CH2:4][CH2:3][OH:2])[CH3:23])=[O:27]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 5247031N-MethylaminoethanolHCID 13004099Chloro 2-phenylacetate

Produkt 1

HCID 133669682-chloro-N-(2-hydroxyethyl)-N-methylbenzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 125 g. (0.73 mol) of O-chlorophenylacetic acid, 155 g. (1.3 mol) of thionyl chloride and 2-3 drops of dimethylformamide in 1500 ml. of toluene was stirred at room temperature for three hours. The toluene was evaporated under reduced pressure to give an oil which was dissolved in 200 ml. of methylenechloride. This was added dropwise to a solution of 165 g. (2.2 mol) of N-methylamino ethanol in 1 liter of methylene chloride. After addition was complete, the solution was stirred at room temperature for three hours. The organic solution was washed with water, dilute hydrochloric acid and saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give 2-chloro-N-(2-hydroxyethyl)-N-methylbenzeneacetamide as a crystalline solid, m.p. 77°.

Aufarbeitung

  1. additionA mixture of 125 g
  2. customThe toluene was evaporated under reduced pressure
  3. customto give an oil which
  4. dissolutionwas dissolved in 200 ml
  5. additionThis was added dropwise to a solution of 165 g
  6. additionAfter addition
  7. washThe organic solution was washed with water, dilute hydrochloric acid and saturated sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cc2a11012b6648aebabbd78fb7e7be00
Quelldatensatz
uspto-grants-1984_08
Patentnummer
US04465677

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