Hydrochloric Acid → Methyl 2-(2,4-difluorophenylamino)-5-fluoro-6-phenylthionicotinate

HRID 232456ノート

反応式

HRID 232456 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:19]=[C:18](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)[C:17]([F:33])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=O.C1([SH:40])C=CC=CC=1.C(N(CC)CC)C.Cl.[CH3:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]>CN(C)C=O.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:19]=[C:18]([C:51]2[CH:50]=[CH:49][CH:54]=[CH:53][CH:52]=2)[C:17]([F:33])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[S:40]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 8058HexaneHCID 8471TriethylamineHCID 13821758Methyl 2-(2,4-difluorophenylamino)-5-fluoro-6-(2,4,6-trimethylbenzenesulfonyloxy)nicotinate

生成物 1

HCID 54549062Methyl 2-(2,4-difluorophenylamino)-5-fluoro-6-phenylthionicotinate収率 90.2%

試薬・触媒・溶媒 3

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

実験手順

In 39 ml of N,N-dimethylformamide was dissolved 3.89 g of methyl 2-(2,4-difluorophenylamino)-5-fluoro-6-(mesitylenesulfonyloxy)nicotinate, and to the resulting solution were added 1.34 g of thiophenol and 1.23 g of triethylamine, after which the resulting mixture was subjected to reaction at room temperature for 5 hours. Subsequently, 120 ml of ethyl acetate and 120 ml of water were added to the reaction mixture, and the pH of the mixture was adjusted to 2.0 with 2N hydrochloric acid. The organic layer was separated, washed successively with 80 ml of water and 80 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 20 ml of n-hexane, after which the crystals thus deposited were collected by filtration to obtain 2.85 g (yield 90.2%) of methyl 2-(2,4-difluorophenylamino)-5-fluoro-6-phenylthionicotinate having a melting point of 126°-128° C. The physical properties of this compound were identical with those of the compound obtained in Example 7.

後処理

  1. customafter which the resulting mixture was subjected to reaction at room temperature for 5 hours
  2. customThe organic layer was separated
  3. washwashed successively with 80 ml of water and 80 ml of saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customto the crystalline material thus obtained
  7. filtrationafter which the crystals thus deposited were collected by filtration

出典と根拠

ORDレコード
ord-dfce6356dc4b4e9b877bc1bfb8a92518
出典データセット
uspto-grants-1989_07
特許番号
US04851535

反応ノート

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