Acetic Acid → 1-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

HRID 2353859

반응식

HRID 2353859 반응식
C(OC([CH:6]1[CH2:12][CH2:11][N:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:9]2[CH:23]=[CH:24][CH:25]=[CH:26][C:8]=2[C:7]1=[O:27])=O)C.CC(O)=O.Cl.[OH-].[Na+]>O>[C:19]1([CH3:22])[CH:18]=[CH:17][C:16]([S:13]([N:10]2[CH2:11][CH2:12][CH2:6][C:7](=[O:27])[C:8]3[CH:26]=[CH:25][CH:24]=[CH:23][C:9]2=3)(=[O:15])=[O:14])=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12435934Ethyl 5-oxo-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate

생성물 1

HCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one수율 60%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To the mixture of 5-Oxo-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester thus obtained, were added AcOH (2.4 l), conc.HCl (800 ml) and H2O (240 ml). The mixture was heated at reflux for 5 h and poured into ice water. The pH was adjusted to about 7-8 by adding diluted aqueous NaOH. The mixture was extracted with CH2Cl2. The organic layer was separated, dried over MgSO4, concentrated, and the residue was crystallized from the mixture (4:1 n-hexane:AcOEt) to give 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one (278 g, 60%) as a white powder.

후처리

  1. customthus obtained
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 5 h
  4. extractionThe mixture was extracted with CH2Cl2
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customthe residue was crystallized from the mixture (4:1 n-hexane:AcOEt)

출처 및 근거

ORD 기록
ord-d15c3884765440dc9dda3779ee3e08de
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749992B2

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