1,2-Dichloroethane → 4-(4-Chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide

HRID 579596

Reaktionsgleichung

Reaktionsgleichung von HRID 579596
C(Cl)CCl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:32][NH:33][O:34][CH3:35].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:35][O:34][N:33]([CH3:32])[C:18]([CH:15]1[CH2:16][CH2:17][CH:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)[CH2:13][CH2:14]1)=[O:20]

Komponenten

9

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

Produkt 1

HCID 885771284-(4-Chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

EDC (3.21 g, 16.8 mmol) was added portionwise to a stirred solution of 4-(4-chlorophenyl)-cyclohexanecarboxylic acid (2.0 g, 8.4 mmol), DMAP (5 mg), HOBt (5 mg) and N,O-dimethylhydroxylamine hydrochloride (1.63 g, 16.8 mmol) in dichloromethane (40 mL). Triethylamine (3.4 g, 4.7 mL, 33.5 mmol) was added dropwise, and the reaction mixture was stirred at room temperature. After stirring overnight the reaction mixture was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 4-(4-chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide as a colorless oil (1.85 g. 78%); MS (+CI): m/z for C15H20ClNO2: expected 281.1. found 282.2 (M+H)+.

Aufarbeitung

  1. stirringAfter stirring overnight the reaction mixture
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b3567bb806dc48f794504e860688111f
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

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