Triethylamine → 2-methyl-N-[4-methyl-2-[2-[(trifluoromethyl)thio]-4-pyrimidinyl]phenyl]propanamide

HRID 1780583노트

반응식

HRID 1780583 반응식
[F:1][C:2](I)([F:4])[F:3].[SH:6][C:7]1[N:12]=[C:11]([C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[CH:10]=[CH:9][N:8]=1.C(N(CC)CC)C>C(#N)C.CCOCC>[CH3:23][CH:22]([CH3:24])[C:21]([NH:20][C:14]1[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[C:11]1[CH:10]=[CH:9][N:8]=[C:7]([S:6][C:2]([F:4])([F:3])[F:1])[N:12]=1)=[O:25]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 16843TrifluoroiodomethaneHCID 178426600HCID 178426600, 화합물

생성물 1

HCID 190470452-methyl-N-[4-methyl-2-[2-[(trifluoromethyl)thio]-4-pyrimidinyl]phenyl]propanamide수율 73.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

2 g trifluoromethyl iodide was condensed into a solution of 0.57 g (0.002 mol) N-[2-(2-mercapto-4-pyrimidinyl)-4-methylphenyl]-2-methylpropanamide and 2.5 g triethylamine in 20 mL anhydrous acetonitrile, and the reaction mixture was stirred under a dry ice condenser while exposed to a sun lamp for 4 h. The reaction mixture was diluted with 100 mL ether and washed successively with water, 1N sodium hydroxide solution, and brine. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.52 g of the title compound as yellow crystals melting at 114°-116° C. 1H NMR (CDCl3): δ 1.21 (d,6H), 2.40 (s,3H), 2.55 (m,1H), 7.40-8.70 (5H), 10.7(s,1H,NH).

후처리

  1. washwashed successively with water, 1N sodium hydroxide solution, and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent

출처 및 근거

ORD 기록
ord-0109d0ca322846629b0e04a49894fff5
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05631206

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