Triethylamine → Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate

HRID 732562

反応式

HRID 732562 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O-:16])=O)[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])([O-:3])=[O:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH2:47]([NH:50][CH2:51][CH2:52][CH3:53])[CH2:48][CH3:49]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:12][O:11][C:9](=[O:10])[C:8]1[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:14]([N:50]([CH2:51][CH2:52][CH3:53])[CH2:47][CH2:48][CH3:49])=[O:16])[CH:7]=1

参加物

8

反応物 5

HCID 8471Triethylamine2 回HCID 8902DipropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6931682Monomethyl-5-nitroisophthalate

生成物 1

HCID 690570Methyl 3-[(dipropylamino)carbonyl]-5-nitrobenzoate収率 90%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Dissolve commercially available monomethyl 5-nitroisophthalate (3.000 g, 14.07 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.238 g, 16.89 mmol), 1-hydroxybenzotriazole hydrate (2.587 g, 16.89 mmol) and 4-dimethylaminopyridine (0.172 g, 1.407 mmol) and triethylamine (5.885 mL, 42.22 mmol) in dichloromethane (309 mL) and stir the mixture at room temperature for 0.5 h. Add dipropylamine (2.026 mL, 14.78 mmol) and triethylamine (5.885 mL, 42.22 mmol) and stir the mixture overnight. Concentrate and redissolve the residue in ethyl acetate and wash with two portions each of 5% aqueous potassium hydrogen sulfate solution, 5% aqueous sodium bicarbonate solution, saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (3.885 g, 90%).

後処理

  1. concentrationConcentrate
  2. dissolutionredissolve the residue in ethyl acetate
  3. washwash with two portions each of 5% aqueous potassium hydrogen sulfate solution, 5% aqueous sodium bicarbonate solution, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

出典と根拠

ORDレコード
ord-d9d73c4313e34cdba5a79bc3eb6cf4d7
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

関連ノート

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