Sodium Carbonate → N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

HRID 2049091

Reaktionsgleichung

Reaktionsgleichung von HRID 2049091
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].[C:33](Cl)([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].S(Cl)([Cl:46])=O>O.C(Cl)(Cl)Cl>[C:33]([N:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:18]1[CH:19]=[CH:20][C:21]([C:22]([Cl:46])=[O:24])=[CH:25][CH:26]=1)([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 24386Thionyl ChlorideHCID 472634-(Hexadecylamino)benzoic acid

Produkt 1

HCID 20437379N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To 15 g. (41.5 m moles) 4-(hexadecylamino)benzoic acid in 200 ml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. (59 m moles) carbobenzyloxy chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1 N hydrochloric acid, dried, and evaporated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. (5 eq) thionyl chloride and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time to yield a viscous, orange oil.

Aufarbeitung

  1. additionTo the vigorously stirred solution is added 10 g
  2. customthe layers are separated
  3. washwashed three times with 1 N hydrochloric acid
  4. customdried
  5. customevaporated to an oil
  6. dissolutionThe oil is dissolved in 300 ml
  7. additiontoluene, treated with 15 ml
  8. customThe solvents are evaporated
  9. dissolutionthe residue is dissolved three times in toluene
  10. customevaporating each time
  11. customto yield a viscous, orange oil

Quellen und Nachweise

ORD-Eintrag
ord-719dcf0947bc4e5183450f61378b0a09
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04196208

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