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2-(Dimethylamino)ethanol → 2-[2-(1,3-benzothiazol-2-yl)-5-nitrophenoxy]-N,N-dimethylethanamine

HRID 339498
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HRID 339498 반응식
[OH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[S:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[O:1][CH2:42][CH2:41][N:40]([CH3:44])[CH3:39]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 1360605262-(2-Hydroxy-4-nitrophenyl)benzothiazole

생성물 1

HCID 673122622-[2-(1,3-benzothiazol-2-yl)-5-nitrophenoxy]-N,N-dimethylethanamine수율 47.1%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

To a stirred mixture of 2-(2-hydroxy-4-nitrophenyl)benzothiazole (0.15 g, 0.55 mmol), triphenylphosphine (0.216 g, 0.825 mmol) and N,N-dimethylethanolamine (0.059 g, 0.66 mmol) in dry THF (10 ml) at 0° C. was added dropwise DIAD (0.167 g, 0.825 mmol). The reaction mixture was stirred at 0° C. for 0.5 h, then left to rise to room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (20:1 DCM/MeOH) to give the title compound (0.089 g, 47%) as a yellow solid.

후처리

  1. waitleft
  2. waitto rise to room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography (20:1 DCM/MeOH)

출처 및 근거

ORD 기록
ord-99059d2f655c49faabc6de36e74bc76c
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895313B2

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