4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

HRID 1038662ノート

反応式

HRID 1038662 の反応式
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].C(N(CC)CC)C.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>ClCCl>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([C:20]([F:19])([F:30])[F:31])[CH:22]=2)=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

参加物

5

反応物 3

HCID 83904-Methyl-3-nitroanilineHCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chloride

生成物 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 4-methyl-3-nitroaniline (5 g, 32.2 mmol, 1.0 eq.) and triethylamine (5.38 ml, 38.6 mmol, 1.2 eq.) in dichloromethane (100 ml) is added a solution of 3-trifluoromethylbenzoyl chloride 33.8 mmol, 1.05 eq.) within 30 min. The suspension formed is stirred for 1 h at room temperature. Then, the reaction mixture is diluted with dichloromethane (800 ml) and extracted with water (100 ml), 2M aqueous Na2CO3 (100 ml), 2M HCl (100 ml), water (100 ml). The organic layer is dried over Na2SO4, evaporated to a volume of about 100 ml and diluted with hexanes (100 ml). The precipitate is filtered off, washed with hexanes/dichloromethane 1:1 and hexanes. Vacuum drying over night at room temperatures gives light yellow fine needles: HPLC: tR=6.72 min (purity: >99%, gradient A), ESI-MS: 325.2 [MH]+

後処理

  1. customThe suspension formed
  2. extractionextracted with water (100 ml), 2M aqueous Na2CO3 (100 ml), 2M HCl (100 ml), water (100 ml)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. customevaporated to a volume of about 100 ml
  5. additiondiluted with hexanes (100 ml)
  6. filtrationThe precipitate is filtered off
  7. washwashed with hexanes/dichloromethane 1:1 and hexanes
  8. customVacuum drying over night at room temperatures
  9. customgives light yellow fine needles

出典と根拠

ORDレコード
ord-7f1ca51656ed403d8d5a940cc47138d5
出典データセット
uspto-grants-2013_10
特許番号
US08552002B2

反応ノート

読み込み中…