Phenyl isocyanate → 10-(N-Phenylcarbamoyl)-1,4,7,10-tetraazacyclododecane

HRID 1654984ノート

反応式

HRID 1654984 の反応式
COC(OC)N(C)C.[NH:9]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O.C(O)C>[C:21]1([NH:27][C:28]([N:9]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

8

反応物 4

HCID 7672Phenyl isocyanateHCID 14798Sodium HydroxideHCID 649631,4,7,10-TetraazacyclododecaneHCID 78373Dimethylformamide dimethyl acetal

生成物 1

HCID 2007734010-(N-Phenylcarbamoyl)-1,4,7,10-tetraazacyclododecane

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

15.9 g (133.5 mmol) of dimethylformamide-dimethylacetal (under nitrogen) is added to 20.0 g (116.1 mmol) of 1,4,7,10-tetraazacyclododecane in 200 ml of absolute toluene. It is refluxed slowly and the solvent is distilled off in this way. Then, it is concentrated by evaporation under reduced pressure. The residue is cooled to 0° C. 16.6 g (139.32 mmol) of phenyl isocyanate is instilled under a nitrogen atmosphere and heated slowly to 100° C. It is stirred for 12 hours at this temperature. It is cooled to room temperature and a mixture of 160 ml of ethanol/40 ml of water is added. Then, it is stirred for 10 minutes at room temperature. Then, 18.58 g (464.4 mmol) of sodium hydroxide is added and it is stirred for 24 hours at 40° C. It is evaporated to dryness in a vacuum and the residue is taken up in 400 ml of water. The aqueous phase is extracted 5 times with 200 ml of methylene chloride, the organic phase is dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel (mobile solvent=methyl-tert-butyl ether/methanol/conc. aqu. ammonia=6/3/1).

後処理

  1. temperatureIt is refluxed slowly
  2. distillationthe solvent is distilled off in this way
  3. concentrationThen, it is concentrated by evaporation under reduced pressure
  4. temperatureheated slowly to 100° C
  5. temperatureIt is cooled to room temperature
  6. additionis added
  7. stirringThen, it is stirred for 10 minutes at room temperature
  8. stirringit is stirred for 24 hours at 40° C
  9. customIt is evaporated to dryness in a vacuum
  10. extractionThe aqueous phase is extracted 5 times with 200 ml of methylene chloride
  11. customthe organic phase is dried on magnesium sulfate
  12. concentrationconcentrated by evaporation in a vacuum
  13. customThe residue is chromatographed on silica gel (mobile solvent=methyl-tert-butyl ether/methanol/conc. aqu. ammonia=6/3/1)

出典と根拠

ORDレコード
ord-df42693429884ce2aef44e46bbd5a9fe
出典データセット
uspto-grants-1995_04
特許番号
US05410043

反応ノート

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