Dicyclohexylcarbodiimide → 1,4-dihydro-4-oxo-N-(2-oxo-1-imidazolidinyl)-5-(phenylmethoxy)-2-pyridinecarboxamide

HRID 1252593ノート

反応式

HRID 1252593 の反応式
[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][NH:5][C:4]([C:16]([OH:18])=O)=[CH:3]1.[NH2:19][N:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.CN(C1C=CC=CN=1)C.ON1C2C=CC=CC=2N=N1>[O:1]=[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][NH:5][C:4]([C:16]([NH:19][N:20]2[CH2:24][CH2:23][NH:22][C:21]2=[O:25])=[O:18])=[CH:3]1

参加物

7

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 1816971-Aminoimidazolidin-2-oneHCID 110539185-(Benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxylic acid

生成物 1

HCID 141824551,4-dihydro-4-oxo-N-(2-oxo-1-imidazolidinyl)-5-(phenylmethoxy)-2-pyridinecarboxamide収率 71.3%

試薬・触媒・溶媒 3

HCID 218852-Dimethylaminopyridine触媒HCID 757711-Hydroxybenzotriazole触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid (12.26 g, 0.05 mol) and 1-amino-2-imidazolidinone (5.56 g, 0.055 mol) were suspended in 120 ml of dimethylformamide. To the suspension was added 0.3 g of dimethylaminopyridine and 0.4 g of N-hydroxybenzotriazole. After stirring for 30 minutes at room temperature, a solution of 11.35 g of dicyclohexylcarbodiimide (0.055 mol) in 50 ml of dimethylformamide was added dropwise and the mixture was stirred overnight at room temperature. The precipitate (dicyclohexylurea) was filtered off and the filtrate evaporated in vacuo. The remaining syrup crystallized on treatment with aqueous sodium bicarbonate, yielding 11.7 g of the title compound, melting point 158°-160° C. An additional crop of 0.8 g of product, melting point 162°-164° C., crystallized from the aqueous filtrate.

後処理

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe precipitate (dicyclohexylurea) was filtered off
  3. customthe filtrate evaporated in vacuo
  4. customThe remaining syrup crystallized on treatment with aqueous sodium bicarbonate

出典と根拠

ORDレコード
ord-85ea2517941343a48c5db604218d5731
出典データセット
uspto-grants-1988_05
特許番号
US04743685

反応ノート

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