3,5-Diaminobenzoic acid → 6-{4-[(1E)-3-(4-pentyloxyphenoxy)-3-oxoprop-1-enyl]phenoxy}hexyl 3,5 diamino-benzoate

HRID 2246018노트

반응식

HRID 2246018 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[O:18])=[CH:11][CH:10]=1.[NH2:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([NH2:42])[CH:41]=1)[C:36]([OH:38])=[O:37]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[NH2:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([NH2:42])[CH:41]=1)[C:36]([O:38][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[O:18])=[CH:11][CH:10]=1)=[O:37]

참가 물질

5

반응물 2

HCID 120623,5-Diaminobenzoic acidHCID 592174574-pentoxyphenyl (2E)-3-{4-(6-chlorohexyloxy)phenyl}acrylate

생성물 1

HCID 592174606-{4-[(1E)-3-(4-pentyloxyphenoxy)-3-oxoprop-1-enyl]phenoxy}hexyl 3,5 diamino-benzoate수율 69.9%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

7.50 g (16.85 mmol) 4-pentoxyphenyl (2E)-3-{4-(6-chlorohexyloxy)phenyl}acrylate, 2.82 g (18.54 mmol) 3,5-diaminobenzoic acid and 0.62 g (1.69 mmol) tetrabutylammonium iodide were dissolved in 80 ml dimethylformamide. 3.00 ml (20.22 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene(1,5-5) (DBU) were added dropwise in the course of 10 minutes. The reaction temperature rose to 30° C. The mixture was then heated at 80° C. for 22 h. The reaction mixture was cooled and then partitioned between ethyl acetate and a saturated sodium bicarbonate solution; the organic phase was washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 1 kg silica gel using cyclohexane:ethyl acetate 1:1 as eluent yielded 6.6 g of 6-{4-[(1E)-3-(4-pentyloxyphenoxy)-3-oxoprop-1-enyl]phenoxy}hexyl 3,5 diamino-benzoate.

후처리

  1. customrose to 30° C
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ethyl acetate
  4. washthe organic phase was washed repeatedly with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-a9ab002286ee488ab4e8b6c5e90c9475
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687118B2

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