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1,3-Propanediamine → 2-(4-n-Butylphenyl)imino-hexahydropyrimidine

HRID 1758509
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HRID 1758509 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=S)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[NH2:14][CH2:15][CH2:16][CH2:17][NH2:18].C(N(CC)CC)C>C(#N)C.[Hg]Cl>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[NH:18][CH2:17][CH2:16][CH2:15][NH:14]2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

6

반응물 3

HCID 4281,3-PropanediamineHCID 8471TriethylamineHCID 1410041-Butyl-4-isothiocyanatobenzene

생성물 1

HCID 1784410032-(4-n-Butylphenyl)imino-hexahydropyrimidine

시약·촉매·용매 2

HCID 24182Mercurous Chloride촉매HCID 6342Acetonitrile용매3회

실험 절차

A solution of 144 g. of 4-n-butylphenylisothiocyanate in 800 ml of acetonitrile is added dropwise in 30 minutes at room temperature to a solution of 95 ml of 1,3-diaminopropane in 450 ml of acetonitrile, while solution is stirred. After 1 hour, 260 ml of triethylamine are added. A solution of 212 g of mercurychloride in 560 ml of acetonitrile is then added while stirring said solution for 1 hour. The reaction mixture is stirred for another 24 hours and then filtered while warm. The solvent is distilled from the filtrate and the residue is mixed with up in methylene chloride and washed with dilute alkaline solution and water. After drying, the methylene chloride is distilled off, the crude 2-(4-n-butylphenyl)iminohexahydropyrimidine being obtained in a yield of 165 g. The product can be purified by a recrystallisation from a mixture of carbon tetrachloride and petroleum ether. A product is obtained with a melting point of 116°-119° C. The product may also be purified by dissolving it in approximately 20% hydrochloric acid, washing the aqueous phase with ether and then making it alkaline again. The thus purified 2-(4-n-butylphenyl)imino-hexahydropyrimidine can be isolated by taking up in ether, drying and distilling the solvent. The thus purified product also has a melting point of 116°-119° C.

후처리

  1. stirringwhile stirring
  2. customfor 1 hour
  3. stirringThe reaction mixture is stirred for another 24 hours
  4. filtrationfiltered
  5. temperaturewhile warm
  6. distillationThe solvent is distilled from the filtrate
  7. additionthe residue is mixed with up in methylene chloride
  8. washwashed
  9. additionwith dilute alkaline solution and water
  10. customAfter drying
  11. distillationthe methylene chloride is distilled off
  12. customthe crude 2-(4-n-butylphenyl)iminohexahydropyrimidine being obtained in a yield of 165 g
  13. customThe product can be purified by a recrystallisation from a mixture of carbon tetrachloride and petroleum ether
  14. customA product is obtained with a melting point of 116°-119° C
  15. customThe product may also be purified
  16. dissolutionby dissolving it in approximately 20% hydrochloric acid
  17. washwashing the aqueous phase with ether

출처 및 근거

ORD 기록
ord-01fc8f69ead446c2a9a2e9dbd242794c
출처 데이터셋
uspto-grants-1983_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04374143

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