Ethylmorpholine → N-[(3-chloro-2-methylphenyl)methyl]-1,3-dimethyl-2-oxo-4-imidazolidinecarboxamide

HRID 2081052ノート

反応式

HRID 2081052 の反応式
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]([OH:9])=O)[N:4]([CH3:10])[C:3]1=[O:11].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:43][C:44]1[C:45]([CH3:52])=[C:46]([CH2:50][NH2:51])[CH:47]=[CH:48][CH:49]=1>ClCCl>[Cl:43][C:44]1[C:45]([CH3:52])=[C:46]([CH2:50][NH:51][C:7]([CH:5]2[CH2:6][N:2]([CH3:1])[C:3](=[O:11])[N:4]2[CH3:10])=[O:9])[CH:47]=[CH:48][CH:49]=1

参加物

7

反応物 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27576713-Chloro-2-methylbenzylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 229866351,3-Dimethyl-2-oxoimidazolidine-4-carboxylic acid

生成物 1

HCID 59252105N-[(3-chloro-2-methylphenyl)methyl]-1,3-dimethyl-2-oxo-4-imidazolidinecarboxamide収率 28.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 1,3-dimethyl-2-oxo-4-imidazolidinecarboxylic acid (6.000 ml, 0.600 mmol) (0.1M solution in dichloromethane) was added the N-ethylmorpholine (0.380 ml, 3.00 mmol), 1-hydroxybenzotriazole hydrate (110 mg, 0.720 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (138 mg, 0.720 mmol), and the reaction stirred at RT under argon for 10 minutes. [(3-Chloro-2-methylphenyl)methyl]amine (103 mg, 0.660 mmol) was then added and the reaction left to stir at RT under argon overnight. The reaction mixture was diluted with dichloromethane (15 ml) and then the solution was washed with saturated sodium hydrogen carbonate solution (20 ml), water (20 ml), 3N citric acid solution (20 ml), brine (20 ml) and then dried over magnesium sulphate. The solvent was evaporated in vacuo. The residue was purified by mass-directed automated HPLC. Fractions containing product were combined and solvent evaporated in vacuo, co-evaporated with diethyl ether to give the N-[(3-chloro-2-methylphenyl)methyl]-1,3-dimethyl-2-oxo-4-imidazolidinecarboxamide as a white solid (50 mg, 26.8% yield). LC/MS [M+H]+=296, retention time=1.96 minutes

後処理

  1. waitthe reaction left
  2. stirringto stir at RT under argon overnight
  3. washthe solution was washed with saturated sodium hydrogen carbonate solution (20 ml), water (20 ml), 3N citric acid solution (20 ml), brine (20 ml)
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified
  7. additionFractions containing product
  8. customsolvent evaporated in vacuo, co-evaporated with diethyl ether

出典と根拠

ORDレコード
ord-86acfc54e8104f4683a14952c7ae5ba6
出典データセット
uspto-grants-2011_04
特許番号
US07932282B2

反応ノート

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