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

HRID 1038662

반응식

HRID 1038662 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-7f1ca51656ed403d8d5a940cc47138d5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552002B2

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