Benzylamine → HCID 25019976、化合物

HRID 1259458ノート

反応式

HRID 1259458 の反応式
CC1C=CC(S(O[CH2:12][CH:13]2[O:18][C:17]3[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCCCCCC>[CH2:26]([NH:33][CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=2[O:15][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

4

反応物 2

HCID 7504BenzylamineHCID 22238110(7-Nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonate

生成物 1

HCID 25019976HCID 25019976、化合物収率 100%

試薬・触媒・溶媒 1

HCID 8900Heptane溶媒

反応条件

温度
95 °C

実験手順

A 200 mL round bottomed flask equipped with a magnetic stir bar is charged with [7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (40.0 g, 110 mmol) and benzylamine (35.2 g, 328 mmol). The mixture is heated to 95° C. for 3 h, and then heating is discontinued. Once the temperature of the solution is 80° C., heptane (300 mL) is added slowly, with rapid stirring. Once the suspension is cooled to rt, the solid is collected by vacuum filtration, and the filter cake is washed several times with heptane and suction dried to give the title compound (32.55 g, 100%) as a yellow powder. LCMS (Basic Method): 1.93 min, 301 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 7.77-7.70 (m, 1H), 7.47-7.18 (m, 6H), 7.10-7.06 (m, 1H), 4.47 (dd, J=2.5, 11.5 Hz, 1H), 4.37-4.29 (m, 1H), 4.15 (dd, J=7.1, 11.5 Hz, 1H), 3.73 (s, 2H), 2.43 (br s, 1H), 2.82-2.70 (m, 2H).

後処理

  1. customA 200 mL round bottomed flask equipped with a magnetic stir bar
  2. temperatureheating
  3. customis 80° C.
  4. temperatureOnce the suspension is cooled to rt
  5. filtrationthe solid is collected by vacuum filtration
  6. washthe filter cake is washed several times with heptane and suction
  7. customdried

出典と根拠

ORDレコード
ord-8c6b007dcd694eedb06bee5202611242
出典データセット
uspto-grants-2013_06
特許番号
US08466296B2

反応ノート

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