Pyridine → 1-(3-(p-Tolyloxy)phenyl)urea

HRID 1592815

反応式

HRID 1592815 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.B(O)(O)[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1.N1C=CC=CC=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Cu+2]>[C:16]1([CH3:19])[CH:17]=[CH:18][C:13]([O:1][C:2]2[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:15]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 12796m-HydroxyphenylureaHCID 79799Tolylboronic acid

生成物 1

HCID 689090341-(3-(p-Tolyloxy)phenyl)urea

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-(3-Hydroxyphenyl)urea (2.00 g), p-tolylboronic acid (3.57 g), and Cu(OAc)2 (2.63 g) were dissolved in 150 mL of THF, and 5.32 mL of pyridine was added. The reaction was stirred at room temperature overnight, then filtered through Celite with the aid of 200 mL EtOAc. The filtrate was washed with water, 0.2N CuSO4, 0.5N NaOH, and brine, and dried over Na2SO4 The solution was concentrated to a solid that was taken up in 200 mL of dichloromethane and stirred at room temperature for about 1 hour, after which time it was filtered to give 1-(3-(p-tolyloxy)phenyl)urea as white solid. The material was used in Step B without further purification.

後処理

  1. filtrationfiltered through Celite with the aid of 200 mL EtOAc
  2. washThe filtrate was washed with water, 0.2N CuSO4, 0.5N NaOH, and brine
  3. dry with materialdried over Na2SO4 The solution
  4. concentrationwas concentrated to a solid
  5. stirringstirred at room temperature for about 1 hour
  6. filtrationafter which time it was filtered

出典と根拠

ORDレコード
ord-20fb2d00de434fcf9b988962e00ffa75
出典データセット
uspto-grants-2007_11
特許番号
US07294616B2

関連ノート

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