4-Nitro-o-anisic acid → 2-(2-Methoxy-4-nitrophenyl)-6-methoxybenzothiazole

HRID 339493

反応式

HRID 339493 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[SH:10].[CH3:11][O:12][C:13]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=1[C:15](O)=O>C(Cl)Cl.CO>[CH3:11][O:12][C:13]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:14]=1[C:15]1[S:10][C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[N:1]=1

参加物

4

反応物 2

HCID 757764-Nitro-o-anisic acidHCID 2355092-Amino-5-methoxybenzene-1-thiol

生成物 1

HCID 672371952-(2-Methoxy-4-nitrophenyl)-6-methoxybenzothiazole収率 84.2%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
150 °C

実験手順

A thoroughly mixed paste of 2-amino-5-methoxybenzenethiol (2.0 g, 12.88 mmol) and 2-methoxy-4-nitrobenzoic acid (2.54 g, 12.88 mmol) in trimethylsilylpolyphosphate (10 ml) was stirred and heated at 150° C. under an atmosphere of argon for 30 min. On cooling to room temperature, the reaction mixture was suspended in DCM/MeOH and an orange solid was collected by filtration. The filtrate was washed with 1 M HCl (2×50 ml), sat. NaHCO3 (2×50 ml), brine (70 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a solid which was combined with that collected and recrystallised from AcOH to give the title compound (3.43 g, 83%) as a yellow solid.

後処理

  1. temperatureOn cooling to room temperature
  2. filtrationan orange solid was collected by filtration
  3. washThe filtrate was washed with 1 M HCl (2×50 ml), sat. NaHCO3 (2×50 ml), brine (70 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customto give a solid which
  7. customthat collected
  8. customrecrystallised from AcOH

出典と根拠

ORDレコード
ord-d0507224f6004267a22b2c908592f5c8
出典データセット
uspto-grants-2014_11
特許番号
US08895313B2

関連ノート

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