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Triethylamine → 4-(5-Azidomethyl-imidazol-1-ylmethyl)-2-(2-chloro-phenoxy)-benzonitrile

HRID 379045
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HRID 379045 반응식
Cl.[Cl:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][C:6]1[CH:13]=[C:12]([CH2:14][N:15]2[C:19]([CH2:20]O)=[CH:18][N:17]=[CH:16]2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:38]=[N+:39]=[N-:40].[Na+]>C(Cl)Cl.CN(C=O)C>[N:38]([CH2:20][C:19]1[N:15]([CH2:14][C:12]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:5][C:4]3[CH:22]=[CH:23][CH:24]=[CH:25][C:3]=3[Cl:2])[CH:13]=2)[CH:16]=[N:17][CH:18]=1)=[N+:39]=[N-:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 216970452-(2-Chloro-phenoxy)-4-(5-hydroxymethyl-imidazol-1-ylmethyl)-benzonitrile Hydrochloride

생성물 1

HCID 216970744-(5-Azidomethyl-imidazol-1-ylmethyl)-2-(2-chloro-phenoxy)-benzonitrile

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(2-chloro-phenoxy)-4-(5-hydroxymethyl-imidazol-1-ylmethyl)-benzonitrile hydrochloride, as described in Example 15, (0.07 g, 0.186 mmol) in CH2Cl2 (4.0 mL), and triethylamine (0.078 mL, 0.558 mmol) at 0° C. was added methanesulfonyl chloride (0.016 mL, 0.205 mmol). The cooling bath was removed and the mixture was stirred for 1 hr. To this solution was added sodium azide (0.018 g, 0.277 mmol) in DMF (1.0 mL). After 1 hr. the reaction mixture was partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title product which was used in the next step without further purification.

후처리

  1. customThe cooling bath was removed
  2. waitAfter 1 hr
  3. customthe reaction mixture was partitioned between EtOAc and saturated NaHCO3 solution
  4. washThe EtOAc layer was washed with H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration in vacuo

출처 및 근거

ORD 기록
ord-34bb426638b7435d8d0ce80fe8f84056
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06297239B1

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