m-Tolyl isocyanate → 2-(3-Methylphenylaminocarbonylamino)eth-1-ylamine

HRID 18053

반응식

HRID 18053 반응식
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3]C(C)(C)C)=O.[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[C:14]([N:18]=C=O)[CH:13]=1>C(#N)C>[CH3:21][C:12]1[CH:13]=[C:14]([NH:18][C:1]([NH:8][CH2:9][CH2:10][NH2:11])=[O:3])[CH:15]=[CH:16][CH:17]=1

참가 물질

4

반응물 2

HCID 69303m-Tolyl isocyanateHCID 187201N-BOC-ethylenediamine

생성물 1

HCID 221388592-(3-Methylphenylaminocarbonylamino)eth-1-ylamine수율 31%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

N-Boc-Ethylene diamine (800 mg, 5 mmol) and m-tolyl isocyanate (665 mg, 5 mmol) were dissolved in acetonitrile and the mixture stirred at room temperature for 4 hrs. Solvent was removed under reduced pressure and the residue absorbed onto silica gel; prior to purification by flash column chromatography (silica, hexane:EtOAc 1:1) to yield the desired compound as a white solid (300 mg, 21%) (MS (+ESI, m/e) 294 (M+H)+). The N-Boc protected compound (300 mg, 1.02 mmol) was dissolved in formic acid (10 ml) and the mixture stirred at room temperature overnight. Excess acid was removed to yield the formate salt of the title compound as a white foam (210 mg).

후처리

  1. customSolvent was removed under reduced pressure
  2. customthe residue absorbed onto silica gel
  3. customprior to purification by flash column chromatography (silica, hexane:EtOAc 1:1)

출처 및 근거

ORD 기록
ord-d1500acbc22c4a919f8bedbbebebaaf2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741328B2

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