Triethylamine → HCID 23568903, Verbindung

HRID 1823239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823239
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:19]=[C:18]([CH2:29][OH:30])[CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C1COCC1.C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[N:19]=[C:18]([CH2:29][O:30][S:32]([CH3:31])(=[O:34])=[O:33])[CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22171056[5-(3,4-Dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]methanol

Produkt 1

HCID 23568903HCID 23568903, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

Triethylamine (3.25 L, 23.3 mol) was added to a solution containing [5-(3,4-dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-methanol (Example 516, 5.18 kg, 14.8 mol) in THF (25.2 L) and toluene (6.3 L) at rt under N2. The reaction mixture was heated to 35° C. and methanesulfonyl chloride (1.82 L, 23.5 mol) was added slowly maintaining the temperature between 35-45° C. The reaction mixture was stirred for an additional 2 h at 45° C. When HPLC analysis indicated the disappearance of the starting material, the reaction mixture was cooled to rt and quenched with 10% aq. NaCl (6.3 L). The organic layer was washed with brine (5.0 L) and the desired mesylate was used in solution in the next synthetic step without isolation. Data compared favorably with that obtained for Example 1, Step D.

Aufarbeitung

  1. temperaturemaintaining the temperature between 35-45° C
  2. temperaturethe reaction mixture was cooled to rt
  3. customquenched with 10% aq. NaCl (6.3 L)
  4. washThe organic layer was washed with brine (5.0 L)
  5. customthat obtained for Example 1, Step D

Quellen und Nachweise

ORD-Eintrag
ord-a46d90a081774cca8e47eb9b07355c48
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037931B2

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