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4-Aminobenzophenone → N-[4-(Phenylcarbonyl)phenyl]-3,3-difluoro-2-hydroxy-2-difluoromethylpropanamide

HRID 327212
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인쇄 미리보기

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HRID 327212 반응식
[F:1][CH:2]([F:11])[C:3]([CH:8]([F:10])[F:9])([OH:7])[C:4](O)=[O:5].C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:24][C:25]1[CH:38]=[CH:37][C:28]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1>O1CCCC1>[C:31]1([C:29]([C:28]2[CH:27]=[CH:26][C:25]([NH:24][C:4](=[O:5])[C:3]([OH:7])([CH:8]([F:10])[F:9])[CH:2]([F:11])[F:1])=[CH:38][CH:37]=2)=[O:30])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 143464-AminobenzophenoneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 222874542,2-Bis-difluoromethyl-2-hydroxyacetic acid

생성물 1

HCID 21480127N-[4-(Phenylcarbonyl)phenyl]-3,3-difluoro-2-hydroxy-2-difluoromethylpropanamide수율 25%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2,2,-bis-difluoromethyl-2-hydroxy-acetic acid (1.76 g, 10 mmole) in tetrahydrofuran (40ml) was added carbonyl diimidazole (0.81 g, 5 mmole). The flask was placed in a sonic bath and the reaction sonicated for 20 minutes followed by addition of 4-aminobenzophenone. The reaction was sonicated for 18 hours. The reaction mixture was filtered and the filtrate evaporated to dryness. The recovered pasty solid was washed with ether and the combined ether washings evaporated. The recovered solid was crystallized from ethyl acetate/hexane to give the title compound (0.89g, 25%) as yellow crystals; mp 139°-142° C. 1H--NMR (300 MHz, d6 --DMSO) : 6.48(t, J=53.7Hz, 2H, HCF2); 7.53-7.77 7H, ArH, OH); 7.95-7.98(m, 3H, ArH); 10.43 (s, 1H, NH). MS(CI,CH4) 356(M+1, 100%).

후처리

  1. customThe flask was placed in a sonic bath
  2. customthe reaction sonicated for 20 minutes
  3. customThe reaction was sonicated for 18 hours
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated to dryness
  6. washThe recovered pasty solid was washed with ether
  7. customthe combined ether washings evaporated
  8. customThe recovered solid was crystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-7477f9b6e0aa4baf820ffd5b0e4f40ca
출처 데이터셋
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05272163

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