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

HRID 1468229노트

반응식

HRID 1468229 반응식
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]3([CH2:21][CH2:20]3)[C:10]2=[N:13]S(C(C)(C)C)=O)=[CH:5][CH:4]=1.C(OCC)C>O1CCOCC1>[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]3([CH2:21][CH2:20]3)[C:10]2=[NH:13])=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86706705N-(7'-Bromo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-1'-ylidene)-2-methylpropane-2-sulfinamide2회

생성물 1

HCID 867067067'-Bromo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalen]-1'-imine수율 85.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

HCl (4 M in 1,4-dioxane) (8.38 mL, 33.5 mmol) was added to a warm solution of N-(7′-bromo-3′,4′-dihydro-1′H-spiro[cyclopropane-1,2′-naphthalene]-1′-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 10, 1.19 g, 3.35 mmol) in dry dioxane (12 mL) under Ar (g). The mixture was stirred at r.t. for 40 min after which diethyl ether was added. The precipitate was filtered and washed with diethyl ether and then taken up in CH2Cl2 and washed twice with sat. aq. NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated to give the title compound (0.717 g, 85% yield). MS (ES+) m/z 250.0 [M+H]+.

후처리

  1. additionwas added
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether
  4. washwashed twice with sat. aq. NaHCO3
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-327990ddbc064184b3fa8d09b7a18566
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000184B2

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