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tert-Butylsulfinamide, (R)-(+)- → (NZ,R)-N-[(4-bromo-2-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 40280
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HRID 40280 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([Cl:10])[CH:3]=1.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:17]\[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])=[C:4]([Cl:10])[CH:3]=1
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참가 물질

5

반응물 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 141091094-Bromo-2-chlorobenzaldehyde

생성물 1

HCID 57691068(NZ,R)-N-[(4-bromo-2-chlorophenyl)methylidene]-2-methylpropane-2-sulfinamide

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 6344Dichloromethane용매

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온도
37 °C

실험 절차

A suspension of 4-bromo-2-chlorobenzaldehyde (1150 mg, 5240 μmol), (r)-(+)-2-methyl-2-propanesulfinamide (1588 mg, 13100 μmol), copper(ii) sulfate (696.4 μl, 15720 μmol) in DCM (10 mL) was stirred at 37° C. for 78 h. Reaction filtered through Celite, and solid washed repeatedly with DCM. Filtrate concentrated then purified on silica (80 g) eluting product with 0>30% of EtOAc/Hex. MS (ESI pos. ion) m/z: 322/324 (MH+). Calc'd exact mass for C11H13BrClNOS: 321/323.

후처리

  1. customReaction
  2. filtrationfiltered through Celite, and solid
  3. washwashed repeatedly with DCM
  4. concentrationFiltrate concentrated
  5. customthen purified on silica (80 g)
  6. washeluting product with 0>30% of EtOAc/Hex

출처 및 근거

ORD 기록
ord-4f79440e739e4ef3b2297af9766d349c
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524900B2

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