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Triphenylphosphine → 3-(2-Aminoethoxy)-5-chloro-1,2-benzisoxazole hydrochloride

HRID 1739051
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HRID 1739051 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(OC([NH:39][CH2:40][CH2:41]O)=O)(C)(C)C.[Cl:43][C:44]1[CH:45]=[CH:46][C:47]2[O:51][N:50]=[C:49]([OH:52])[C:48]=2[CH:53]=1>O1CCCC1>[ClH:43].[NH2:39][CH2:40][CH2:41][O:52][C:49]1[C:48]2[CH:53]=[C:44]([Cl:43])[CH:45]=[CH:46][C:47]=2[O:51][N:50]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 178518984HCID 178518984, 화합물

생성물 1

HCID 186960233-(2-Aminoethoxy)-5-chloro-1,2-benzisoxazole hydrochloride수율 186.9%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of triphenylphosphine (0.87 g) in tetrahydrofuran (10 ml), was added diethyl azodicarboxylate (0.57 g) dropwise with stirring under ice cooling. The reaction mixture was stirred at the same temperature for 10 minutes. Then, 2-(N-t-butoxycarbonylamino)ethanol (0.48 g) and 5-chloro-3-hydroxy-1,2-benzisoxazole (0.51 g) were added to the reaction mixture successively and stirred under ice cooling for 10 minutes and at room temperature for 24 hours. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (4/1) as an eluent. The title compound (0.70 g) was obtained as colorless crystals by crystallization from isopropylether.

후처리

  1. stirringThe reaction mixture was stirred at the same temperature for 10 minutes
  2. stirringstirred under ice cooling for 10 minutes and at room temperature for 24 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (4/1) as an eluent

출처 및 근거

ORD 기록
ord-aa9773a961de4a86884dff87b7605d24
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05965591

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