1,1'-Carbonyldiimidazole → HCID 66813314、化合物

HRID 1891269ノート

反応式

HRID 1891269 の反応式
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH2:8][C:9]([NH:11][CH:12]2[CH2:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].C(=O)(O)[O-].[Na+]>C(#N)C.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][C:9](=[O:10])[N:11]([CH:12]3[CH2:13][CH2:14]3)[C:17]2=[O:18])=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 43401847HCID 43401847、化合物

生成物 1

HCID 66813314HCID 66813314、化合物収率 98%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-(4-bromobenzylamino)-N-cyclopropylacetamide (7H4) (28.3 mmol, 8.0 g) in acetonitrile (200 ml) was added carbonyldiimidazole (56.5 mmol, 9.16 g) and 4-dimethylaminopyridine (56.5 mmol, 6.90 g). The reaction mixture was heated to 60° C. and stirred overnight before cooling to room temperature. Saturated sodium bicarbonate solution was added and the mixture extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated and the residue purified on silica eluting with heptane/acetone 9:1 to 7:3 to give 1-(4-bromobenzyl)-3-cyclopropylimidazolidine-2,4-dione (7H5) 8.3 g (98%); 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 2H) 7.13 (d, 2H) 4.50 (s, 2H) 3.66 (s, 2H) 2.62 (m, 1H) 0.97 (d, 4H).

後処理

  1. temperaturebefore cooling to room temperature
  2. extractionthe mixture extracted with EtOAc (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue purified on silica eluting with heptane/acetone 9:1 to 7:3

出典と根拠

ORDレコード
ord-98400514268b4f7c99803e7ba30e9c19
出典データセット
uspto-grants-2013_08
特許番号
US08507521B2

反応ノート

読み込み中…