Benzyl Bromide → HCID 19008945, 화합물

HRID 1742426노트

반응식

HRID 1742426 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:6]=[CH:5]2.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[CH2:16]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][CH:6]=[CH:5]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 79394N-(6-hydroxynaphthalen-1-yl)acetamide

생성물 1

HCID 19008945HCID 19008945, 화합물수율 61.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of N-(6-hydroxy-naphthalen-1-yl)-acetamide (5.72 grams, 28 mmol), benzyl bromide (4.78 grams, 28 mmol) and potassium carbonate (4.14 grams, 30 mmol) in DMF (50 mL) was stirred at room temperature for 20 hours. The reaction was diluted with ether (250 mL) and was washed with saturated aqueous NaHCO3 (2×30 mL) and saturated aqueous NaCl (2×30 mL), dried MgSO4) and concentrated in vacuo. The crude residue was azeotroped with heptane (2×100 mL) to give a colored solid. The solid was filtered and washed with hexanes to give 5.0 grams of a colorless product. 1NMR (250 MHz, CDCl3): d 7.25 (m, 11 H), 4.4 (s, 2 H), 2.16 (s, 3 H).

후처리

  1. washwas washed with saturated aqueous NaHCO3 (2×30 mL) and saturated aqueous NaCl (2×30 mL), dried MgSO4) and
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was azeotroped with heptane (2×100 mL)
  4. customto give a colored solid
  5. filtrationThe solid was filtered
  6. washwashed with hexanes

출처 및 근거

ORD 기록
ord-bd7185c76dfa48c3a2cf1eae134ba42a
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05338740

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