n-Heptyl isocyanate → Methyl 3-[3'-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate

HRID 250832

反応式

HRID 250832 の反応式
[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1.O1CCCC1.C(N(CC)CC)C>O>[CH3:11][N:12]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[C:9]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:10]

参加物

5

反応物 3

HCID 138341n-Heptyl isocyanateHCID 67273433Methyl 3-(3'-methylaminobiphenyl-4-yl)propanoateHCID 68616177Triethylamine tetrahydrofuran

生成物 1

HCID 67272234Methyl 3-[3'-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

1.2 mL (7.43 mmol, 2 eq) of heptyl isocyanate are added to a solution of 1.0 g (3.7 mmol, 1 eq) of methyl 3-(3′-methylaminobiphenyl-4-yl)propanoate (obtained as in 4c) in 15 mL of a 4/1 tetrahydrofuran/triethylamine mixture. The reaction mixture is stirred for 12 hours at 40° C. The reaction is stopped by addition of 10 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.15 g of methyl 3-[3′-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate are obtained. Yield=76%

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-800f07e77d51499d8878a360cbebb2cd
出典データセット
uspto-grants-2011_01
特許番号
US07863332B2

関連ノート

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