Hydrochloric Acid → N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide

HRID 84467

反応式

HRID 84467 の反応式
C([Li])CCC.Br[C:7]1[S:20][C:10]2[C:11]3[CH:19]=[N:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30].Cl.C([O-])(O)=O.[Na+]>CCCCCC.O1CCCC1>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29]([C:7]1[S:20][C:10]2[C:11]3[CH:19]=[N:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:30]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 76833Chlorophenyl isocyanateHCID 516892Sodium BicarbonateHCID 579000912-Bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepineHCID 178418339Butyllithium

生成物 1

HCID 57900340N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide収率 66.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

1.6 M of n-Butyllithium in hexane (0.6302 mL) was added dropwise to a solution of 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (0.227 g, 0.804 mmol) in tetrahydrofuran (6.00 mL, 74.0 mmol) at −75° C. The dark brown mixture was stirred at −78° C. for 20 min. 1-Chloro-2-isocyanato-benzene (0.1421 g, 0.9252 mmol) in 2 ml of tetrahydrofuran was added dropwise and the mixture was kept at −78° C. for 20 min. 4N aq. HCl (1 ml) was added and the mixture was poured into 50 ml of sat. aq NaHCO3. The mixture was extracted twice with methylene chloride, combined, and washed with water and brine, and dried over MgSO4. After concentrating under vacuum, the residue was triturated with ethyl acetate. The collected precipitate was N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide (0.19 g, 66% yield). MS (ESI+) 357.0.

後処理

  1. waitthe mixture was kept at −78° C. for 20 min
  2. extractionThe mixture was extracted twice with methylene chloride
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentrating under vacuum
  6. customthe residue was triturated with ethyl acetate

出典と根拠

ORDレコード
ord-3cf032983782437b91bd33540e20162c
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

読み込み中…