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

HRID 18053

反応式

HRID 18053 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 221388592-(3-Methylphenylaminocarbonylamino)eth-1-ylamine収率 31%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d1500acbc22c4a919f8bedbbebebaaf2
出典データセット
uspto-grants-2010_06
特許番号
US07741328B2

関連ノート

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