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

HRID 556354ノート

反応式

HRID 556354 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c747789c82d94f079eb4aaf867528a28
出典データセット
uspto-grants-2011_11
特許番号
US08058276B2

反応ノート

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