Ammonia → 1-(2,3-Ethylenedioxy-5-sulfamoylbenzoyl)-4-(2-pyrimidinyl)-piperazine

HRID 2052618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2052618
[S:1]([C:5]1[CH:6]=[C:7]([C:15]([OH:17])=O)[C:8]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:14]=1)(=[O:4])(=[O:3])[NH2:2].O1CCOCC1.[N:24]1[CH:29]=[CH:28][CH:27]=[N:26][C:25]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.N>O.C(N(CC)CC)C>[CH2:12]1[CH2:11][O:10][C:9]2[C:8](=[C:7]([CH:6]=[C:5]([S:1](=[O:3])(=[O:4])[NH2:2])[CH:14]=2)[C:15]([N:33]2[CH2:34][CH2:35][N:30]([C:25]3[N:24]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:31][CH2:32]2)=[O:17])[O:13]1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 887471-(2-Pyrimidinyl)piperazineHCID 205447607-Sulfamoyl-2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

Produkt 1

HCID 205447391-(2,3-Ethylenedioxy-5-sulfamoylbenzoyl)-4-(2-pyrimidinyl)-piperazineAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

146 g of 7-sulfamoyl-1,4-benzodioxane-5-carboxylic acid, 300 ml of dioxane and 57 g of triethylamine were introduced into a 1-liter 3-neck flask provided with an agitator, a thermometer and an introduction funnel. The mixture was heated to 40°-50° C. and 80 ml of water was added. The solution was cooled to a temperature of from 5°-10° C. and 61.5 g of ethyl chloroformiate was added. Agitation of the mixture was maintained for one hour at 10° C. and 93 g of 1-(2-pyrimidinyl)-piperazine was added without the temperature rising above 15° C. Agitation of the mixture was continued for one hour at ambient temperature and then, after the addition of 1,500 ml of water, the mixture was rendered alkaline to a pH of 10 with ammonia. The crystals produced after distillation under vacuum of the solvents and cooling were dried off, washed with water, dried in a drying oven at 50° C. and then purified by treatment with 120 ml of chloroform. After filtration and drying, 92 g of 1-(2,3-ethylenedioxy-5-sulfamoylbenzoyl)-4-(2-pyrimidinyl)-piperazine was produced (M.P.: 239° C.; yield: 40.2%). The structure was confirmed by nuclear magnetic resonance.

Aufarbeitung

  1. customprovided with an agitator
  2. temperatureThe mixture was heated to 40°-50° C.
  3. temperatureThe solution was cooled to a temperature of from 5°-10° C. and 61.5 g of ethyl chloroformiate
  4. additionwas added
  5. customrising above 15° C
  6. customThe crystals produced
  7. distillationafter distillation under vacuum of the solvents
  8. temperaturecooling
  9. customwere dried off
  10. washwashed with water
  11. customdried in a drying oven at 50° C.
  12. custompurified by treatment with 120 ml of chloroform
  13. filtrationAfter filtration
  14. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-47f4d1ba6cb0485180c0e85d18a2e303
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04186135

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