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4-Chloro-3-nitrobenzoic acid → 2-Methyl-1,3-benzothiazole-5-carboxylic acid

HRID 1498958
ノート
印刷プレビュー

反応式

HRID 1498958 の反応式
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-])=O.O.O.O.O.O.O.O.O.O.[S-2:23].[Na+].[Na+].C(O[C:30](=O)[CH3:31])(=O)C>C(OCC)(=O)C.O.C(O)(=O)C>[CH3:31][C:30]1[S:23][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N:11]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 73204-Chloro-3-nitrobenzoic acidHCID 7918Acetic AnhydrideHCID 73972Sodium sulfide nonahydrate

生成物 1

HCID 6499532-Methyl-1,3-benzothiazole-5-carboxylic acid収率 80%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

4-Chloro-3-nitrobenzoic acid (2.02 g, 10.00 mmol), sodium sulfide nonahydrate (7.22 g, 30.00 mmol) and water (5 ml) were suspended, and the mixture was heated at about 100° C. for 30 minutes. After being allowed to cool, the mixture was cooled by ice, and acetic anhydride (18 ml) and acetic acid (10 ml) were added to the mixture. The resulting mixture was heated under reflux for 2 hours and stirred at a room temperature for 15 hours. To the mixture, tap water and then ethyl acetate were added, and sulfur was removed by filtration. The ethyl acetate layer was washed with a saturated saline solution, and then dried over anhydrous magnesium sulfate and concentrated to give the title compound (1.54 g, 80%) as a light-yellow powder.

後処理

  1. temperatureto cool
  2. additionwere added to the mixture
  3. temperatureThe resulting mixture was heated
  4. temperatureunder reflux for 2 hours
  5. customsulfur was removed by filtration
  6. washThe ethyl acetate layer was washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-0b5aa2b412a340c1bda4f6fd0695096c
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09200008B2

反応ノート

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