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

HRID 1262996
ノート
印刷プレビュー

反応式

HRID 1262996 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 131768926-Amidino-2-naphthyl 4-dimethylaminobenzoate収率 20.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d53944763a8f48aaa18b0b9f62ef74da
出典データセット
uspto-grants-1984_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04454338

反応ノート

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