Diclofenac → 4-Carbamoylphenyl 2-[2-(2,6-dichlorophenylamino)-phenyl]acetate

HRID 44161

반응식

HRID 44161 반응식
[CH:1]1[CH:2]=[CH:3][C:4]([NH:11][C:12]2[C:13]([Cl:19])=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=1.OC1C2N=NNC=2C=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.O[C:46]1[CH:54]=[CH:53][C:49]([C:50]([NH2:52])=[O:51])=[CH:48][CH:47]=1>CN(C)C=O.C(Cl)(Cl)Cl>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[NH:11][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH2:7][C:8]([O:10][C:46]1[CH:54]=[CH:53][C:49]([C:50](=[O:51])[NH2:52])=[CH:48][CH:47]=1)=[O:9]

참가 물질

7

반응물 4

HCID 3033DiclofenacHCID 10868DicyclohexylcarbodiimideHCID 650524-HydroxybenzamideHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 593455914-Carbamoylphenyl 2-[2-(2,6-dichlorophenylamino)-phenyl]acetate수율 17%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To the solution of 1 (diclofenac, 890 mg, 3.0 mmol) in 50 mL of N,N-dimethylformamide, hydroxybenzotriazole (445 mg, 3.3 mmol) and DCC (680 mg, 3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (4, 616 mg, 4.5 mmol) was added and stirred for 1 h at 0° C. and 3 hs at room temperature. After filtration, the filtrate was evaporated under reduced pressure and the oily residue thus obtained was dissolved in chloroform; the organic layer was washed with brine, dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 5 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (5) was obtained (212 mg, 17% yield).

후처리

  1. stirringstirred for 1 h at 0° C.
  2. customat room temperature
  3. filtrationAfter filtration
  4. customthe filtrate was evaporated under reduced pressure
  5. customthe oily residue thus obtained
  6. washthe organic layer was washed with brine
  7. dry with materialdried on anhydrous MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. washeluted with CH2Cl2/MeOH (9/1), from which 4-carbamoylphenyl 2-(2-(2,6-dichlorophenylamino)phenyl)acetate (5)
  11. customwas obtained (212 mg, 17% yield)

출처 및 근거

ORD 기록
ord-e02319aa71c74df7a7d37a8e358774bf
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541398B2

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