Dicyclohexylcarbodiimide → N-[(4,6-dimethoxypyrimidin-2-yl)carbonyl]-2-methoxycarbonylbenzenesulfonamide

HRID 344582

Reaktionsgleichung

Reaktionsgleichung von HRID 344582
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH2:14])(=[O:13])=[O:12])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[N:35]=[C:34]([C:40](O)=[O:41])[N:33]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[N:35]=[C:34]([C:40]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([O:2][CH3:1])=[O:4])(=[O:13])=[O:12])=[O:41])[N:33]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 42546Benzoic acid, 2-(aminosulfonyl)-, methyl esterHCID 44224834,6-Dimethoxypyrimidine-2-carboxylic acid

Produkt 1

HCID 14580647N-[(4,6-dimethoxypyrimidin-2-yl)carbonyl]-2-methoxycarbonylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2.2 g of 2-methoxycarbonylbenzenesulfonamide are added in portions at 0° C. to 2° C. to a mixture of 2.3 g of dicyclohexylcarbodiimide, 120 mg of 4-dimethylaminopyridine and 2.2 g of 4,6-dimethoxypyrimidine-2-carboxylic acid in 80 ml of absolute dichloromethane. The mixture is stirred for 0.5 hour at 0° C. and 2 hours at room temperature, and allowed to stand overnight. The urea which has precipitated is filtered off, the filtrate is concentrated in vacuo, and the residue is stirred for 0.5 hour with 100 ml of 2 N sodium carbonate solution. The aqueous phase is extracted using ether, and a pH of 2-3 is established using concentrated hydrochloric acid. The product which has precipitated is filtered off with suction and dried in vacuo. This gives 1.3 g of N-(4,6-dimethoxypyrimidin-2-yl)carbonyl]-2-methoxycarbonylbenzenesulfonamide of melting point 163°-165° C. (from ethyl acetate).

Aufarbeitung

  1. waitto stand overnight
  2. customThe urea which has precipitated
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated in vacuo
  5. stirringthe residue is stirred for 0.5 hour with 100 ml of 2 N sodium carbonate solution
  6. extractionThe aqueous phase is extracted
  7. customThe product which has precipitated
  8. filtrationis filtered off with suction
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0015cf6429ba4281ae343ec9520b699d
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053072

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