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

HRID 232456노트

반응식

HRID 232456 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dfce6356dc4b4e9b877bc1bfb8a92518
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851535

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