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

HRID 2246018ノート

反応式

HRID 2246018 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a9ab002286ee488ab4e8b6c5e90c9475
出典データセット
uspto-grants-2010_03
特許番号
US07687118B2

反応ノート

読み込み中…