Potassium Carbonate → 3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide

HRID 491639노트

반응식

HRID 491639 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12]C([O-])(C)C.[K+].Cl[C:19]1[CH:24]=[CH:23]N=[C:21]([C:25]([NH:27][CH3:28])=[O:26])[CH:20]=1.C([O-])([O-])=O.[K+].[K+].C[NH-]>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:19]2[CH:20]=[C:21]([CH:12]=[CH:23][CH:24]=2)[C:25]([NH:27][CH3:28])=[O:26])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

참가 물질

8

반응물 5

HCID 11430Potassium CarbonateHCID 14768144-Chloro-N-methylpicolinamideHCID 37588824-Amino-3-NitrophenolHCID 21952893MethylamideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 690175323-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

A solution of 4-amino-3-nitrophenol (0.6 g, 3.84 mmol, 1.2 eq) in DMSO (2.75 mL, 5×) was treated with KOt-Bu (0.44 g, 3.84 mmol, 1.2 eq), and the mixture was stirred at RT for 2 h. The contents were treated with 4-chloro-N-methyl-2-pyridinecarboxamide (0.55 g, 3.2 mmol, 1.0 eq), K2CO3 (0.24 g, 1.7 mmol, 0.53 eq), and heated at 110° C. for 16 h. HPLC showed N-methylamide <2%. To the stirred mixture was added water (about 30 mL) slowly, and the compound precipitated. The solid was filtered off (slow filtration) and washed with water (about 60 mL). The filtrant was dried in a vacuum oven over night to give the title compound as a brown solid.

후처리

  1. temperatureheated at 110° C. for 16 h
  2. customthe compound precipitated
  3. filtrationThe solid was filtered off
  4. filtration(slow filtration)
  5. washwashed with water (about 60 mL)
  6. customThe filtrant was dried in a vacuum oven over night

출처 및 근거

ORD 기록
ord-65335709b7e648d9b0ec1adb116c1d19
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531553B2

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