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

HRID 1780583ノート

反応式

HRID 1780583 の反応式
[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]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 16843TrifluoroiodomethaneHCID 178426600HCID 178426600、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0109d0ca322846629b0e04a49894fff5
出典データセット
uspto-grants-1997_05
特許番号
US05631206

反応ノート

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