Hydrochloric Acid → HCID 178485344, 화합물

HRID 661661노트

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HRID 661661 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]#[N:20])[CH3:8])=[O:6].[N:25]([Sn](CCCC)(CCCC)CCCC)=[N+:26]=[N-:27].C([Al](CC)CC)C.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([CH3:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]1[NH:27][N:26]=[N:25][N:20]=1)=[O:6]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 16682930TriethylaluminumHCID 686031543-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide

생성물 1

HCID 178485344HCID 178485344, 화합물수율 87.4%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide (2.0 g, 4.9 mmol), azidotributyltin (4.03 mL, 14.7 mmol) and triethylaluminum (7.74 mL, 14.7 mmol, 25% in toluene) in toluene (25 mL) was heated at 80° C. for 5 hrs. The mixture was allowed to cool to room temperature and was acidified with 1N HCl. The mixture was extracted with DCM. The organic layer was washed with water and brine, and was dried. The filtrate was concentrated in vacuo and the residue purified by silica gel column chromatography (eluent: 3% MeOH in DCM) to afford 3-bromo-4-chloro-N-methyl-N-{2-[3-(1H-tetrazol-5-yl)-propoxy]-phenyl}-benzamide (1.93 g). MS [M+H]+: 451.9; tR=2.26 min. (method 1)

후처리

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with DCM
  3. washThe organic layer was washed with water and brine
  4. customwas dried
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by silica gel column chromatography (eluent: 3% MeOH in DCM)

출처 및 근거

ORD 기록
ord-4d2d3b3201044cea8ecccbcda5dfa4c5
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084614B2

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