N,N,N',N'-Tetramethylmethanediamine → 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazole

HRID 36949

반응식

HRID 36949 반응식
C(OC(=O)C)(=O)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][C:17]2[S:21][C:20]([C:22]([F:25])([F:24])[F:23])=[N:19][CH:18]=2)=[CH:11][CH:10]=1.CN(C[N:31]([CH3:33])C)C.[NH2:34]N>C(Cl)(Cl)Cl.FC(F)(F)C(O)=O.ClCCl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([C:17]3[S:21][C:20]([C:22]([F:25])([F:24])[F:23])=[N:19][CH:18]=3)[CH2:33][NH:31][N:34]=2)=[CH:11][CH:10]=1

참가 물질

8

반응물 4

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 9321HydrazineHCID 152392244-Fluorophenyl-2-(2-Trifluoromethyl-5-Thiazolyl)Ethanone

생성물 1

HCID 152392404,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazole

시약·촉매·용매 3

HCID 6422Trifluoroacetic acid촉매HCID 6212Chloroform용매2회HCID 6344Dichloromethane용매

실험 절차

A solution of 112 uL (microliters) (1.1 mmol) of acetic anhydride and 289 mg (milligram) (1.0 mmol) of 1-(4-fluorophenyl)-2-(2-trifluoromethyl-5-thiazolyl)ethanone in 2 mL of chloroform was added to a solution of 136 uL (12 mmol) of N,N,N',N',-tetramethyldiaminomethane in 3 mL of chloroform with stirring over a 5-min period. The resulting solution was stirred for 10 min and then 46 uL (1.5 mmol) of anhydrous hydrazine and one drop of trifluoroacetic acid were added sequentially. The mixture was heated at reflux with stirring for 20-30 min and then was cooled and diluted to 20 mL with dichloromethane. The resulting solution was washed with 2×10 mL of water, dried over sodium sulfate, and filtered to obtain 4,5-dihydro-3-(4-fluorophenyl)-4-(2-trifluoromethyl-5-thiazolyl)-1H-pyrazole. 4-Trifluoromethylphenyl isocyanate (143 uL, 1.0 mmol) was then added and the mixture was heated at reflux for 15 min, cooled, and concentrated by evaporation under reduced pressure. The residue was purified by medium pressure liquid chromatography eluting with a 90:10 mixture of hexane and ether to obtain 297 mg (63. percent of theory) of the title compound as a white foamy solid. An analytical sample prepared by recrystallization from a mixture of hexane and acetone was a white solid melting at 174°-176° C.

후처리

  1. stirringThe resulting solution was stirred for 10 min
  2. temperatureThe mixture was heated
  3. temperatureat reflux
  4. stirringwith stirring for 20-30 min
  5. temperaturewas cooled
  6. washThe resulting solution was washed with 2×10 mL of water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-8e2ad4bf9e73461fa3e6d38c8cbfdf01
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418247

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