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

HRID 1468232노트

반응식

HRID 1468232 반응식
[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

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 86706708N-(7'-Bromo-4-methoxy-3',4'-dihydro-1'H-spiro[cyclohexane-1,2'-naphthalene]-1'-ylidene)-2-methylpropane-2-sulfinamide2회

생성물 1

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

실험 절차

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+.

후처리

  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

출처 및 근거

ORD 기록
ord-652ff472bbea48dcad6d6ec9cb6c4aae
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000184B2

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