Dimethyl Sulfoxide → 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal

HRID 2404993

反応式

HRID 2404993 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:13]1[N:14]([CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=1)[CH3:12].C(N(CC)CC)C>ClCCl>[CH2:11]([C:13]1[N:14]([CH2:26][CH2:27][CH2:28][CH:29]=[O:30])[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=1)[CH3:12]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 689965274-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol

生成物 1

HCID 866266434-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal収率 100.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Under a nitrogen atmosphere, dimethylsulfoxide (3.6 mL, 1.5 eq.) and oxalyl chloride (3.5 mL, 1.1 eq.) were sequentially added dropwise to chilled (dry ice/acetone bath) dichloromethane (100 mL). A solution of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (10 g, 37 mmol, 1 eq.) in dichloromethane was added dropwise. Triethylamine (15.5 mL, 3 eq.) was added. The ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. After about 2 hours analysis by TLC indicated that the reaction was complete. The reaction mixture was diluted with dichloromethane (175 mL) and water (200 mL) and made basic (pH 10) with aqueous 5% sodium carbonate. The organic layer was washed sequentially with water (2×200 mL) and brine (150 mL) and then concentrated under reduced pressure to provide 9.9 g of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal.

後処理

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with dichloromethane (175 mL) and water (200 mL)
  3. washThe organic layer was washed sequentially with water (2×200 mL) and brine (150 mL)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a7310def4c1848dea55c9d98d05de177
出典データセット
uspto-grants-2014_08
特許番号
US08802853B2

関連ノート

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