Hydrochloric Acid → 7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-imine

HRID 1468232ノート

反応式

HRID 1468232 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:23][CH2:22][CH:21]([O:24][CH3:25])[CH2:20][CH2:19]3)[C:9]2=[N:12]S(C(C)(C)C)=O)=[CH:4][CH:3]=1.Cl>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:23][CH2:22][CH:21]([O:24][CH3:25])[CH2:20][CH2:19]3)[C:9]2=[NH:12])=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 86706708N-(7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalene]-1'-ylidene)-2-methylpropane-2-sulfinamide2 回

生成物 1

HCID 867067097'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalen]-1'-imine収率 76%

実験手順

To N-(7′-bromo-4-methoxy-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-naphthalene]-1′-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 13, 0.610 g, 1.43 mmol) under N2 (g) was added HCl (4 M in 1,4-dioxane, 3.58 mL, 14.3 mmol). The mixture was stirred at r.t. for 45 min and was then concentrated. DCM (approx. 2 mL) was added followed by Et2O. A solid formed and was filtered off and washed with Et2O. The solid was dissolved in DCM. NaHCO3 (sat. aq.) was added and the mixture was poured into a phase separator. The organic phase was collected and concentrated to give the title compound (0.35 g, 76% yield): MS (EI) m/z 321 M+.

後処理

  1. concentrationwas then concentrated
  2. additionDCM (approx. 2 mL) was added
  3. customA solid formed
  4. filtrationwas filtered off
  5. washwashed with Et2O
  6. dissolutionThe solid was dissolved in DCM
  7. additionNaHCO3 (sat. aq.) was added
  8. additionthe mixture was poured into a phase separator
  9. customThe organic phase was collected
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-652ff472bbea48dcad6d6ec9cb6c4aae
出典データセット
uspto-grants-2015_04
特許番号
US09000184B2

反応ノート

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