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

HRID 491639ノート

反応式

HRID 491639 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-65335709b7e648d9b0ec1adb116c1d19
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

反応ノート

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