Tetramethyl orthocarbonate → 6-(1-Butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-2-hydroxybenzimidazole

HRID 276082

Reaktionsgleichung

Reaktionsgleichung von HRID 276082
[CH2:1]([S:5]([NH:8][C:9](=[O:27])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[CH:11]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[CH3:28][O:29]C(OC)(OC)OC>C(O)(=O)C>[CH2:1]([S:5]([NH:8][C:9]([C:10]1[CH:15]=[CH:14][C:13]2[N:16]=[C:28]([OH:29])[N:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[C:12]=2[CH:11]=1)=[O:27])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 74613Tetramethyl orthocarbonateHCID 18315556Benzamide,4-amino-n-(butylsulfonyl)-3-[[(2,4-dichlorophenyl)methyl]amino]-

Produkt 1

HCID 1784556586-(1-Butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-2-hydroxybenzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 0.220 mg of N-1-butanesulfonyl-4-amino-3-(2,4-dichlorobenzylamino)benzamide, 0.3 ml of tetramethoxymethane and 2.0 ml of acetic acid was stirred at 60° C. for 4 hours. Acetic acid was distilled off under reduced pressure, and the residue was extracted with chloroform and with water. The chloroform layer was concentrated, and 4.0 ml of methanol and 36% hydrochloric acid (4 drops) were added to the residue. The mixture was stirred at 60° C. for 2 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The crystals precipitated were washed with water, and were dried to give 0.207 g of 6-(1-butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-2-hydroxybenzimidazole (379).

Aufarbeitung

  1. distillationAcetic acid was distilled off under reduced pressure
  2. extractionthe residue was extracted with chloroform and with water
  3. concentrationThe chloroform layer was concentrated
  4. addition4.0 ml of methanol and 36% hydrochloric acid (4 drops) were added to the residue
  5. stirringThe mixture was stirred at 60° C. for 2 hours
  6. customThe crystals precipitated
  7. washwere washed with water
  8. customwere dried

Quellen und Nachweise

ORD-Eintrag
ord-faf80ac69ee141c385ac07307c3a6662
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352985B1

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