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1,2-Dibromoethane → 1-Benzylthio-2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzene

HRID 1939612
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HRID 1939612 반응식
[OH-].[K+].Cl.[NH2:4]O.[CH2:6]([S:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].BrCCBr>CO>[CH2:6]([S:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]1[O:18][CH2:19][CH2:24][O:27][N:4]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
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참가 물질

7

반응물 5

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 775668Benzoic acid, 2-[(phenylmethyl)thio]-, methyl ester

생성물 1

HCID 221041471-Benzylthio-2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzene수율 21.2%

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
40 °C

실험 절차

160 g (2.86 mol) of potassium hydroxide in 700 ml of methanol are added dropwise, at room temperature, to a mixture of 98.7 g (1.42 mol) of hydroxylamine hydrochloride and 700 ml of methanol. Subsequently, 184 g (0.712 mol) of methyl 2-(benzylthio)benzoate are added in portions at room temperature. The mixture is stirred at 40° C. overnight. 98.1 g (0.712 mol) of potassium carbonate are then added, 601 g (3.20 mol) of 1,2-dibromoethane are added dropwise, and the mixture is left stirring at 60° C. overnight. Subsequently, the solvent is distilled off under reduced pressure. The residue is partitioned between methylene chloride and water. The organic phase is dried and the solvent is distilled off under reduced pressure. The residue is stirred up with absolute ethyl alcohol. The solid is filtered off with suction and dried under high vacuum. 43.1 g (21% of theory) of 1-benzylthio-2-(5,6-dihydro-[1,4,2]-dioxazin-3-yl)benzene are obtained as a pale yellow solid. Melting point: 73°-77° C.

후처리

  1. waitthe mixture is left
  2. stirringstirring at 60° C. overnight
  3. distillationSubsequently, the solvent is distilled off under reduced pressure
  4. customThe residue is partitioned between methylene chloride and water
  5. customThe organic phase is dried
  6. distillationthe solvent is distilled off under reduced pressure
  7. stirringThe residue is stirred up with absolute ethyl alcohol
  8. filtrationThe solid is filtered off with suction
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-100118ea4d22424ebc442eb03511fc14
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05696257

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