Dicyclohexylamine → Dicyclohexylcarbamoyl chloride

HRID 1066702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066702
[CH:1]1([NH:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:14][C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl.[OH:26][N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C:28]1=[O:33].[CH:34]1([NH:40][C:41](Cl)=[O:42])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>N1C=CC=CC=1.O>[CH:8]1([N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:15]([Cl:14])=[O:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.[CH:34]1([N:40]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:41]([O:26][N:27]2[C:31](=[O:32])[CH2:30][CH2:29][C:28]2=[O:33])=[O:42])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Komponenten

8

Edukt 4

HCID 7582DicyclohexylamineHCID 80170N-HydroxysuccinimideHCID 94429TriphosgeneHCID 22252134N-Cyclohexylcarbamoyl chloride

Produkt 2

HCID 222909Dicyclohexylcarbamoyl chlorideHCID 15538723N-(dicyclohexylcarbamoyloxy)succinimide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

According to the procedure described in H. Eckert et al., Angew. Chem. Int. Ed. Engl. 26, 894-895 (1987), dicyclohexylcarbamoyl chloride was synthesized from dicyclohexylamine and triphosgene [chemical name: bis(trichloromethyl)carbonate]. N-hydroxysuccinimide (5.3 g, 0.05 mol) was dissolved in 100 g of sufficiently dried pyridine. To the solution was added dropwise 13.7 g (0.05 mol) of cyclohexylcarbamoyl chloride. After stirring at room temperature overnight, the reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, decolored with active carbon and then concentrated. The deposited crystal was filtered and washed with a small amount of ether to obtain 4.6 g of N-(dicyclohexylcarbamoyloxy)succinimide represented by the following formula. Yield: 31.0%

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. filtrationThe deposited crystal was filtered
  6. washwashed with a small amount of ether

Quellen und Nachweise

ORD-Eintrag
ord-2b777fda8dd847b68244cb18d63dfe8a
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245478B1

Notizen zur Reaktion

Wird geladen…