Triethylamine → HCID 71530104、化合物

HRID 1887826ノート

反応式

HRID 1887826 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.Cl.[CH3:19][NH:20][O:21][CH3:22].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:20]([O:21][CH3:22])[CH3:19])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 217338394-Fluoro-2-(phenylamino)benzoic acid

生成物 1

HCID 71530104HCID 71530104、化合物収率 79%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-fluoro-2-phenylamino-benzoic acid (10 g, 43.2 mmol) in DMF (100 mL) was added O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluorophosphate (HBTU) (32.8 g, 86.5 mmol), N,O-dimethylhydroxylamine hydrochloride (5.3 g, 86.5 mmol), and triethylamine (26.0 g, 36.2 mL, 259 mmol) at room temp. The resulting mixture was stirred for 24 hr at room temperature. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with water and brine. The organic layer was dried over anhydrous Na2SO4 and volatiles were removed under reduced pressure. The crude material was purified using silica gel column chromatography (100% hexanes ramped to 30% ethyl acetate in hexanes). Further purification was accomplished by recrystallization from 10% ethyl acetate in petroleum ether. The product 4-fluoro-N-methoxy-N-methyl-2-phenylamino-benzamide (9.35 g, 79%) was obtained as an off-white solid.

後処理

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4 and volatiles
  3. customwere removed under reduced pressure
  4. customThe crude material was purified
  5. customFurther purification
  6. customwas accomplished by recrystallization from 10% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-cb6e215697d64555a50007b8709fc71f
出典データセット
uspto-grants-2013_08
特許番号
US08501732B2

反応ノート

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