Triethylamine → 6-Methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

HRID 556354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556354
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7]([C:10]([OH:12])=O)=[N:8][S:9][C:5]=2[CH:4]=1.[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24].CCN(CC)CC.CCCP(=O)=O>CN(C=O)C.CCOC(C)=O.O>[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:10]([C:7]2[C:6]3[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[S:9][N:8]=2)=[O:12])=[CH:18][C:17]=1[C:23]([F:24])([F:25])[F:26]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 16167369Propylphosphoric anhydride2×HCID 666368056-Methoxybenzo[d]isothiazole-3-carboxylic acid

Produkt 1

HCID 669929426-Methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

209 mg (1.00 mMol) 6-methoxy-benzo[d]isothiazole-3-carboxylic acid (preparation see: WO 2004/029050, Procedure N), 269 mg (1.5 mMol) 4-fluoro-3-trifluoromethyl-aniline and 1.4 ml (10 mMol) Et3N are dissolved in 5 ml of dry DMF and cooled in an ice-bath. Then a solution of 1.17 ml (50% in DMF; 2.0 mMol) propylphosphonic anhydride is added. The mixture is stirred for 15 h at rt, when another 0.58 ml of propylphosphonic anhydride are added. After 2 h, the reaction mixture is poured into water and EtOAc, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and partially concentrated. Addition of hexane precipitates the title compound: m.p.: 157° C.; MS: [M+1]+=371.

Aufarbeitung

  1. temperaturecooled in an ice-bath
  2. waitAfter 2 h
  3. customthe aq. phase separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed twice with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationpartially concentrated
  8. additionAddition of hexane
  9. customprecipitates the title compound

Quellen und Nachweise

ORD-Eintrag
ord-c747789c82d94f079eb4aaf867528a28
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058276B2

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