(2,4-Dichlorophenoxy)Acetic Acid → 2-(2,4-dichlorophenoxy)-N-(3-hydroxyphenyl)acetamide

HRID 1945399ノート

反応式

HRID 1945399 の反応式
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[NH2:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.F[P-](F)(F)(F)(F)F.[PH4+].C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)=[O:8]

参加物

6

反応物 4

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 115683-AminophenolHCID 81531DiisopropylethylamineHCID 21584439Phosphonium hexafluorophosphate

生成物 1

HCID 8366682-(2,4-dichlorophenoxy)-N-(3-hydroxyphenyl)acetamide収率 99%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the (2,4-dichloro-phenoxyacetic acid (600 mg, 2.71 mmol) and 3-amino-phenol (592 mg, 5.43 mmol) in DMF (20.0 mL) were added benzotriazol-1-yl-N-oxy-trispyrrolidino)-phosphonium hexafluorophosphate (PyBOP) (2.8 g, 5.43 mmol), and N,N-diisopropylethylamine (DIPEA) (0.95 ml, 5.43 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4anh), and concentrated. Purification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=10:3:1) gave 2-(2,4-Dichloro-phenoxy)-N-(3-hydroxy-phenyl)-acetamide as a white solid (837 mg, 99% yield)

後処理

  1. custompartitioned between ethyl acetate and brine
  2. customThe organic phase was dried (MgSO4anh)
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (n-Hexane:EtOAc:MeOH=10:3:1)

出典と根拠

ORDレコード
ord-b6d58ca94fb24d9e8d0677a351e8b2d2
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

反応ノート

読み込み中…