N,N-Dimethylaniline → HCID 60077508, Verbindung

HRID 751570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751570
C(Cl)(=O)C=O.[F:6][C:7]1[C:8]([O:18][CH3:19])=[C:9](/[CH:14]=[CH:15]\[CH2:16][OH:17])[C:10]([F:13])=[CH:11][CH:12]=1.C[N:21](C)[C:22]1[CH:27]=CC=CC=1.CC[N:31](CC)CC.[OH2:36]>C(Cl)Cl>[N+:21](=[CH:22][C:27]([O:17][CH2:16]/[CH:15]=[CH:14]\[C:9]1[C:10]([F:13])=[CH:11][CH:12]=[C:7]([F:6])[C:8]=1[O:18][CH3:19])=[O:36])=[N-:31]

Komponenten

7

Edukt 5

HCID 949N,N-DimethylanilineHCID 962WaterHCID 8471TriethylamineHCID 12550982HCID 12550982, VerbindungHCID 60077543HCID 60077543, Verbindung

Produkt 1

HCID 60077508HCID 60077508, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The p-toluenesulfonylhydrozone of glyoxylic acid chloride (5.16 g; 0.02 mol) was added to a solution of (2Z)-3-(3,6-difluoro-2-methoxyphenyl)-2-propen-1-ol (3.6 g; 0.018 mol) in dry CH2Cl2 (50 ml) at −5 C, and N,N-dimethylaniline (2.5 ml; 0.02 mol) was added slowly. After stirring for 30 min at −5 C, Et3N (12 ml; 0.09 mol) was added slowly. The resulting mixture was stirred for 15 min at −5 C and then for 30 min at room temperature, whereupon water (˜50 ml) was added. The organic phase was separated washed with water, brine and concentrated in vacuo. Flash chromatography (silica, EA:Hex; 1:15) gave 3.86 g (80%) of product as a yellow solid.

Aufarbeitung

  1. additionwas added slowly
  2. additionwas added slowly
  3. waitfor 30 min at room temperature
  4. customThe organic phase was separated
  5. washwashed with water, brine
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b0e460c755da4c1fa098b3866f8ebe94
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405310B2

Notizen zur Reaktion

Wird geladen…