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

HRID 1498958
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HRID 1498958 반응식
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
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참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매
2회
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0b5aa2b412a340c1bda4f6fd0695096c
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09200008B2

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