Methanol → HCID 86590716、化合物

HRID 479847

反応式

HRID 479847 の反応式
N[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14].[C:15]([CH2:17][C:18]([O:20]CC)=O)#N.[C:23](OCC)(=O)[CH2:24][C:25]([CH3:27])=O.[NH:32]1CCN[CH2:34][CH2:33]1.[N+]([O-])(O)=O.[CH3:42][OH:43]>O.CN(C)C=O>[NH:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:27][CH2:25][CH2:24][CH2:23][C:17]2[C:18](=[O:20])[NH:32][CH:33]=[CH:34][CH:15]=2)[C:42]1=[O:43]

参加物

9

反応物 6

HCID 887MethanolHCID 944Nitric AcidHCID 4837PiperazineHCID 7764Ethyl cyanoacetateHCID 8868Ethyl AcetoacetateHCID 177271,12-Dodecanediamine

生成物 1

HCID 86590716HCID 86590716、化合物収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 1,12-diaminododecane (100.1 grams, 0.50 mol; obtained from Sigma-Aldrich Co.) and ethyl cyanoacetate (135.2 grams, 128 milliliters, 1.20 mol; obtained from Spectrum Chemicals, New Brunswick, N.J.), in a 2 liter flask was stirred and heated at 150° C. for 1 hour, after which time the amine had been completely converted to the bis(cyanoacetate) as indicated by 1H-NMR analysis. Ethyl acetoacetate (383 milliliters, 3.00 mol; obtained from Lonza Group, Germany), piperazine (172 grams, 2.00 mol; obtained from Spectrum Chemicals), and dimethyl formamide (300 milliliters) were then added to the reaction mixture and the mixture was heated at 120° C. for 4 hours. The resultant pale brown solution was then cooled to 25° C. and was poured into a mixture of methanol (1,500 milliliters), water (500 milliliters), and concentrated (70 percent) nitric acid (300 grams, 258 milliliters, 4.0 mol). A precipitate formed at once. The suspension was stirred overnight, followed by filtration and washing of the solid with 5×500 milliliter portions of 75:25 (volume ratio) of a methanol-water mixture and subsequent drying at 60° C. to give 198 grams (85 percent yield) of dodecamethylene dipyridone as a cream-white solid, which decomposed without melting at 210° C.

後処理

  1. temperaturethe mixture was heated at 120° C. for 4 hours
  2. temperatureThe resultant pale brown solution was then cooled to 25° C.
  3. customA precipitate formed at once
  4. stirringThe suspension was stirred overnight
  5. filtrationfollowed by filtration
  6. washwashing of the solid with 5×500 milliliter portions of 75:25 (volume ratio) of a methanol-water mixture
  7. customsubsequent drying at 60° C.

出典と根拠

ORDレコード
ord-43a988572a2441e993daf97bc3a060ef
出典データセット
uspto-grants-2003_11
特許番号
US06646111B1

関連ノート

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