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

HRID 1939612
ノート
印刷プレビュー

反応式

HRID 1939612 の反応式
[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
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 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-100118ea4d22424ebc442eb03511fc14
出典データセット
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05696257

反応ノート

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