Benzyl Bromide → HCID 19008945、化合物

HRID 1742426ノート

反応式

HRID 1742426 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 19008945HCID 19008945、化合物収率 61.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bd7185c76dfa48c3a2cf1eae134ba42a
出典データセット
uspto-grants-1994_08
特許番号
US05338740

反応ノート

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