Toluene → 7-Fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17313ノート

反応式

HRID 17313 の反応式
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.[CH3:20][O:21][CH2:22][C:23]([O:25][C:26]1[C:27]([F:42])=[C:28]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:29]([CH3:35])=[C:30]([C:33]#[N:34])[C:31]=1[NH2:32])=O>C(OCC)(=O)C>[F:42][C:27]1[C:28]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:29]([CH3:35])[C:30]([C:33]#[N:34])=[C:31]2[C:26]=1[O:25][C:23]([CH2:22][O:21][CH3:20])=[N:32]2

参加物

5

反応物 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 866308254-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl methoxyacetate

生成物 1

HCID 685851157-Fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 79.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

p-Toluenesulfonic acid monohydrate (38 mg, 0.2 mmol) was added to a toluene (30 ml) solution of 4-amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl methoxyacetate (I-58) (214 mg, 0.68 mmol), followed by stirring for 3 hours and a half with heating under reflux. After cooling to room temperature, the reaction liquid was diluted with ethyl acetate, washed with saturated sodium bicarbonate water and saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure to obtain the entitled compound (160 mg, 79%) as a pale yellow solid.

後処理

  1. temperaturea half with heating
  2. temperatureunder reflux
  3. customthe reaction liquid
  4. washwashed with saturated sodium bicarbonate water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration under reduced pressure
  7. concentrationthe eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-433faaa8360747c4866bfea78d305049
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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