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

HRID 732562

반응식

HRID 732562 반응식
[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

참가 물질

8

반응물 5

HCID 8471Triethylamine2회HCID 8902DipropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6931682Monomethyl-5-nitroisophthalate

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d9d73c4313e34cdba5a79bc3eb6cf4d7
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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