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

HRID 1945399노트

반응식

HRID 1945399 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-b6d58ca94fb24d9e8d0677a351e8b2d2
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

반응 노트

불러오는 중…