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Dicyclohexylcarbodiimide → 6-Amidino-2-naphthyl 4-dimethylaminobenzoate

HRID 1262996
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HRID 1262996 반응식
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:45])[NH2:44])[CH:39]=2)[CH:34]=1)(=O)=O>N1C=CC=CC=1>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[C:38]([C:43](=[NH:44])[NH2:45])[CH:39]=3)[CH:34]=2)=[O:8])=[CH:5][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 120924-(Dimethylamino)benzoic acidHCID 130505606-Carbamimidoylnaphthalen-2-yl methanesulfonate

생성물 1

HCID 131768926-Amidino-2-naphthyl 4-dimethylaminobenzoate수율 20.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To 50 ml of dried pyridine, were added 2.9 g of 4-dimethylaminobenzoic acid and 4.4 g of DCC. The mixture was stirred for 30 minutes while being cooled in ice. After adding 5.0 g of 6-amidino-2-naphthol methanesulfonate, the mixture was further stirred for one hour under cooling in ice, then overnight at room temperature. The reaction mixture was filtered, the collected precipitate was washed with pyridine and ethyl ether and heated in DMF. The insolubles were filtered off and the filtrate was mixed with ethyl ether. The precipitate which was formed was collected by filtration and recrystallized from a mixture of methanol and ethyl ether to obtain 1.2 g of a white powder of 6-amidino-2-naphthyl 4-dimethylaminobenzoate methanesulfonate.

후처리

  1. temperaturewhile being cooled in ice
  2. stirringthe mixture was further stirred for one hour
  3. temperatureunder cooling in ice
  4. customovernight
  5. customat room temperature
  6. filtrationThe reaction mixture was filtered
  7. washthe collected precipitate was washed with pyridine and ethyl ether
  8. temperatureheated in DMF
  9. filtrationThe insolubles were filtered off
  10. additionthe filtrate was mixed with ethyl ether
  11. customThe precipitate which was formed
  12. filtrationwas collected by filtration
  13. customrecrystallized from a mixture of methanol and ethyl ether

출처 및 근거

ORD 기록
ord-d53944763a8f48aaa18b0b9f62ef74da
출처 데이터셋
uspto-grants-1984_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04454338

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