Triethylamine → 1-(3-Diethylaminopropyl)-3-[4-(2-methyl-4-nitrophenoxy)pyridin-2-yl]urea

HRID 492692ノート

反応式

HRID 492692 の反応式
[CH3:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.C(N(CC)CC)C.Cl[C:27](OC1C=CC=CC=1)=[O:28].[CH2:36]([N:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][NH2:42])[CH3:37]>O1CCCC1.CN(C)C=O>[CH2:36]([N:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][NH:42][C:27]([NH:11][C:7]1[CH:6]=[C:5]([O:4][C:3]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:2]=2[CH3:1])[CH:10]=[CH:9][N:8]=1)=[O:28])[CH3:37]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 61011N,N-Diethyl-1,3-propanediamineHCID 231530654-(2-Methyl-4-nitrophenoxy)pyridin-2-amine

生成物 1

HCID 231530731-(3-Diethylaminopropyl)-3-[4-(2-methyl-4-nitrophenoxy)pyridin-2-yl]urea収率 96.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(2-methyl-4-nitrophenoxy)pyridin-2-ylamine and triethylamine (500 mg) in tetrahydrofuran (50 ml) was added phenyl chloroformate (0.384 ml, 4.08 mmol) dropwise while stirring in an ice bath, followed by stirring for 0.5 hr. The reaction mixture was concentrated under a reduced pressure to give a residue, to which N,N-dimethylformamide (20 ml) and N,N-diethyl-1,3-propanediamine (1.28 ml) were then added, followed by stirring at room temperature for 2 hrs. The reaction mixture was partitioned between ethyl acetate (150 ml) and water (100 ml). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1, then ethyl acetate) to provide the titled compound (794 mg, 96.9%) as a pale yellow oil.

後処理

  1. stirringby stirring for 0.5 hr
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. customto give a residue
  4. stirringby stirring at room temperature for 2 hrs
  5. customThe reaction mixture was partitioned between ethyl acetate (150 ml) and water (100 ml)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. customThe resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent

出典と根拠

ORDレコード
ord-d5caec6914cf4733bff85e01025693b9
出典データセット
uspto-grants-2009_05
特許番号
US07531532B2

反応ノート

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