Sodium Carbonate → HCID 57435849、化合物

HRID 30546ノート

反応式

HRID 30546 の反応式
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15]C=2)=O)=[CH:6][CH:5]=1.[O:21]1[CH2:26]COCC1.Cl.[CH3:28][NH:29][C:30]([NH2:32])=[NH:31].C([O-])([O-])=O.[Na+].[Na+]>O.CCO>[NH2:32][C:30]1[N:29]([CH3:28])[C:26](=[O:21])[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:1])[F:20])=[CH:9][CH:8]=2)([C:11]2[CH:13]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:31]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 57435846HCID 57435846、化合物HCID 178485118HCID 178485118、化合物

生成物 1

HCID 57435849HCID 57435849、化合物収率 94%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

Into a mixture of 1-[4-(difluoromethoxy)phenyl]-2-phenylethane-1,2-dione (3.7 g, 13.4 mmol), dioxane (180 mL) and EtOH (240 mL) were added 1-methylguanidine hydrochloride (6.6 g, 60.3 mmol), and a solution of Na2CO3 (6.4 g, 60.3 mmol) in H2O (20 mL). The new mixture was stirred at 95° C. for 3 hours. Then, the volatiles were removed under vacuum and the residue was taken in water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification on silica gel (ISCO) using MeOH/EtOAc (1/20) as the eluting solvent gave 2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-phenyl-3,5-dihydro-4H-imidazol-4-one as a white solid (3.65 g, 94% yield). MS m/e (M+H)+ 332; 1H NMR (400 MHz, DMSO-d6) 2.93 (s, 3H), 6.61 (brs, 2H), 7.1 (d, J=8.54 Hz, 2H), 7.15-7.31 (m, 4H), 7.38 (m, 2H), 7.42 (d, J=8.54 Hz, 2H).

後処理

  1. customThen, the volatiles were removed under vacuum
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification on silica gel (ISCO)

出典と根拠

ORDレコード
ord-d5c0ab4c9b4247f1ab127963ddfff5ac
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

反応ノート

読み込み中…