Hexanoyl chloride → 4-Methyl-5-hexanoyl-4-imidazolin-2-one

HRID 247606

反応式

HRID 247606 の反応式
[CH3:1][C:2]1[NH:3][C:4](=[O:7])[NH:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:12](Cl)(=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:1][C:2]1[NH:3][C:4](=[O:7])[NH:5][C:6]=1[C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

参加物

5

反応物 3

HCID 67340Hexanoyl chlorideHCID 709351,3-dihydro-4-methyl-2H-imidazol-2-oneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 135805614-Methyl-5-hexanoyl-4-imidazolin-2-one収率 31%

試薬・触媒・溶媒 1

HCID 7416Nitrobenzene溶媒

反応条件

温度
75 °C

実験手順

A flask equipped with mechanical stirrer, reflux condenser and nitrogen inlet, was charged with 5.0 g (0.051 mol) of 4-methyl-4-imidazolin-2-one in 40 ml of nitrobenzene and cooled to ice-bath temperature. Aluminum chloride (27.1 g, 0.204 mol) was added portionwise. The reaction was heated to 75° C. and 7.55 g (0.056 mol) of hexanoyl chloride was added dropwise over 1 hour. Heating was continued for an additional 5 hours whereupon all starting material had been consumed as evidenced by tlc analysis (silica gel, methanol/ethyl acetate 1:4, phosphomolybdic acid visualization). The reaction was poured onto 100 ml of ice containing 7.5 g of sodium carbonate dissolved in 25 ml of water. The reaction mixture was stirred rapidly while 100 ml of ether were added. The resulting solids were isolated by filtration to afford after drying 5.2 g of crude ketone. The crude solids were recrystallized from 50 ml of water/ethanol 1:1 to afford 3.1 g ( 31%) of homogeneous title product; m.p. 221°-223° C.; IR (KBr) cm-1 : 3178 (s), 3153 (s), 3106 (s), 1746 (s), 1714 (s), 1657 (s), 1644 (s), 1611 (s); 1H-NMR (DMSO-d6): 10.17 (s, 2, N--H), 2.5 (m), 2.27 (s, 3), 1.34 (m, 6), 0.86 (t, 3); 13C-NMR (DMSO-d6): 188.5, 152.4, 118.9, 129.4, 38.8, 31.0, 23.4, 22.0, 13.8, 11.7; mass spectrum (70 eV) m/e 196 (parent), 140 C6H8O2,base), 125 (C5H5N2O2).

後処理

  1. customA flask equipped with mechanical stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. temperaturecooled to ice-bath temperature
  4. temperatureHeating
  5. customhad been consumed
  6. additionThe reaction was poured onto 100 ml of ice containing 7.5 g of sodium carbonate
  7. dissolutiondissolved in 25 ml of water
  8. additionwere added
  9. customThe resulting solids were isolated by filtration
  10. customto afford
  11. dry with materialafter drying 5.2 g of crude ketone
  12. customThe crude solids were recrystallized from 50 ml of water/ethanol 1:1

出典と根拠

ORDレコード
ord-0da206c7cd244f85af88c13fae856f0d
出典データセット
uspto-grants-1987_11
特許番号
US04709044

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