Hexane → 4-chloro-N-methoxy-N-methyl-2-phenylamino-benzamide

HRID 1887779

反応式

HRID 1887779 の反応式
[Cl: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)C(C)C)(C)C.CCCCCC>CN(C=O)C.C(OCC)(=O)C>[Cl: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

7

反応物 4

HCID 8058HexaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 6153344-Chloro-2-(phenylamino)benzoic acid

生成物 1

HCID 866720574-chloro-N-methoxy-N-methyl-2-phenylamino-benzamide収率 56.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of 4-chloro-2-phenylamino-benzoic acid (10.1 g, 41.0 mmol) in DMF (200 mL) was added O-benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluorophosphate (HBTU, 31.2 g, 82.0 mmol), N,O-dimethyl-hydroxylamine hydrochloride (7.94 g, 82.0 mmol), and N,N-diisopropylethylamine (45.0 g, 350.0 mmol) at room temperature. The resulting mixture was stirred for 24 hr. at room temperature. Completion of the reaction was confirmed by silica TLC (mobile phase; hexane:ethyl acetate=7:3; Rf=0.5). The reaction mixture was diluted with ethyl acetate (600 mL) and the organic layer was washed with water (4×200 mL) and brine (200 mL). The organic layer was dried over anhydrous Na2SO4 and volatiles were removed under reduced pressure. The crude material was purified over silica gel (100-200 mesh) column chromatography, using gradient polarity mobile phase (ethyl acetate:hexane=1:9-1:4), to give 4-chloro-N-methoxy-N-methyl-2-phenylamino-benzamide (6.62 g, 56.4% yield) as a yellow solid. 1H NMR (DMSO-d6) δ ppm 7.93 (s, 1H) 7.20-7.39 (m, 3H) 7.02-7.17 (m, 3H) 6.88-6.99 (m, 2H) 3.50 (s, 3H) 3.20 (s, 3H). MS calcd. for C15H15ClN2O2 [(M+H)+] 291.0, obsd. 291.0, [(M-C2H6NO)+] 230.0, obsd. 230.0.

後処理

  1. customat room temperature
  2. washthe organic layer was washed with water (4×200 mL) and brine (200 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4 and volatiles
  4. customwere removed under reduced pressure
  5. customThe crude material was purified over silica gel (100-200 mesh) column chromatography

出典と根拠

ORDレコード
ord-1ba02ab243e74bb29276d331981087c3
出典データセット
uspto-grants-2013_08
特許番号
US08501732B2

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