Triphenylphosphine → N,N-Diethyl-N-[3-((6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolyl)oxy)propyl]amine

HRID 1433509ノート

反応式

HRID 1433509 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[S:14][C:15]1[S:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1.[CH2:23]([N:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28]O)[CH3:24].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.CS(C)=O.CN1CCCC1=O.O1CCCC1>[CH2:23]([N:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([S:14][C:15]3[S:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1])[CH3:24]

参加物

9

反応物 4

HCID 11776TriphenylphosphineHCID 121593-(Diethylamino)-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1359899586-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinol

生成物 1

HCID 58931471N,N-Diethyl-N-[3-((6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolyl)oxy)propyl]amine収率 74.7%

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

6-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinol (500 mg), 3-diethylaminopropanol (290 mg), diethyl azodicarboxylate (390 mg), triphenylphosphine (590 mg), tetrahydrofuran (30 ml), 1-methyl-2-pyrrolidinone (2 ml) and dimethylsulfoxide (10 ml) were stirred together at 0° C. for 5 hours and then at room temperature for 10 hours. Water was added, extraction was performed with ethyl acetate, and the extract was back extracted with 2N aqueous hydrochloric acid. After adding 5N aqueous sodium hydroxide to the hydrochloric acid extract and performing extraction with ethyl acetate, the extract was washed with water and then with brine and dried over magnesium sulfate. NH type silica gel was coated onto a glass filter, the ethyl acetate layer was passed through the filter, and the solvent was distilled off under reduced pressure to obtain 500 mg of a reddish-brown oil.

後処理

  1. extractionextraction
  2. extractionthe extract was back extracted with 2N aqueous hydrochloric acid
  3. additionAfter adding 5N aqueous sodium hydroxide to the hydrochloric acid
  4. extractionextract
  5. extractionextraction with ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialwith brine and dried over magnesium sulfate
  8. filtrationfilter
  9. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-62d6c27507f24470a3efeeae7d2ffc8d
出典データセット
uspto-grants-2009_11
特許番号
US07612092B2

反応ノート

読み込み中…