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2,5-Dimethyl-1,3-benzoxazol-6-amine → 2-Amino-5-(m-dioctadecylcarbamoylbenzenesulfonamido)-p-cresol hydrochloride

HRID 647226
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 647226
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[N:6]=C(C)[O:8][C:4]=2[CH:3]=1.[CH2:13]([N:31]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[C:32](=[O:43])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([S:39]([Cl:42])(=[O:41])=[O:40])[CH:34]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>N1C=CC=CC=1.ClCCl>[ClH:42].[NH2:6][C:5]1[C:4]([OH:8])=[CH:3][C:2]([NH:1][S:39]([C:35]2[CH:36]=[CH:37][CH:38]=[C:33]([C:32](=[O:43])[N:31]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:34]=2)(=[O:41])=[O:40])=[C:11]([CH3:12])[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 204858572,5-Dimethyl-1,3-benzoxazol-6-amineHCID 204858833-(Dioctadecylcarbamoyl)benzene-1-sulfonyl chloride

Produkt 1

HCID 204858602-Amino-5-(m-dioctadecylcarbamoylbenzenesulfonamido)-p-cresol hydrochlorideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 6-amino-2,5-dimethylbenzoxazole (14.8 g, 0.1 mol) in 100 ml of pyridine and 500 ml of dichloromethane was added N,N-dioctadecyl-3-chlorosulfonylbenzamide (72.4 g, 0.1 mol). The mixture was stirred overnight and then washed with water, 10 percent aqueous hydrochloric acid and again with water. To the organic layer was added 10 ml of hydrochloric acid, 300 ml of water and 1000 ml of THF. The mixture was stirred overnight and the precipitate collected, washed with acetonitrile and nearly dried. The damp filter cake was placed in 2 liters of THF and 50 ml of concentrated hydrochloric acid and refluxed 2 hours. The mixture was concentrated to an oil and triturated with one liter of acetonitrile to yield 77.5 g (90 percent) of the product.

Aufarbeitung

  1. washwashed with water, 10 percent aqueous hydrochloric acid and again with water
  2. additionTo the organic layer was added 10 ml of hydrochloric acid, 300 ml of water and 1000 ml of THF
  3. stirringThe mixture was stirred overnight
  4. customthe precipitate collected
  5. washwashed with acetonitrile
  6. customnearly dried
  7. temperature50 ml of concentrated hydrochloric acid and refluxed 2 hours
  8. concentrationThe mixture was concentrated to an oil
  9. customtriturated with one liter of acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-e48d67ee87cf4e0da7720534815dfd34
Quelldatensatz
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04407930

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