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Hydrochloric Acid → 4-amino-N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]benzamide;dihydrochloride

HRID 1711375
ノート
印刷プレビュー

反応式

HRID 1711375 の反応式
[ClH:1].Cl.[NH2:3][C:4](=[N:6]/[N:7]=[C:8](/[C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[CH:13]=[CH:14][CH:15]=1)\[CH3:9])[NH2:5].CCO.Cl>[Fe].O>[ClH:1].[ClH:1].[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]([NH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10](/[C:8](=[N:7]/[N:6]=[C:4]([NH2:5])[NH2:3])/[CH3:9])[CH:11]=2)=[O:27])=[CH:23][CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 87307446N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]-4-nitrobenzamide;dihydrochloride

生成物 1

HCID 873068154-amino-N-[3-[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]benzamide;dihydrochloride収率 212.2%

試薬・触媒・溶媒 2

HCID 23925Iron
触媒
HCID 962Water溶媒

実験手順

To a refluxing suspension of amide F4 (2.02 g, 5.36 mmol) in 2:1 EtOH:H2O (100 mL) were sequentially added Fe dust (1.20 g, 21.44 mmol) and c.HCl (2 mL), and the resulting suspension was refluxed for 14 h. After this time, the hot reaction mixture was filtered through a pad of Celite, and the solvent was removed under reduced pressure. The residue was re-dissolved in hot H2O, and the resulting suspension filtered through a pad of Celite. Solvent was removed under reduced pressure, and the residue dried via three MeOH-azeotrope cycles. The resulting residue was reprecipitated from acidified MeOH to afford triamine F5 (2.18 g, quantitative) as an amorphous cream solid; 1H NMR (400 MHz, DMSO): δ 11.30 (s, 1H, hydrazonyl-N30—H), 10.05 (s, 1H, ArC(O)NHAr), 8.21 (s, 1H, ArH), 8.20-7.55 (m, 8H, ArH & ═C(NH2)2), 7.36 (t, J=7.90 Hz, 1H, ArH), 6.91 (d, J=7.96 Hz, 1H, ArH), 5.30 (v br s, 3H, ArNH3+), 2.35 (s, 3H, Ar(CH3)═N—); LCMS (APCl+): 311 (100%).

後処理

  1. filtrationAfter this time, the hot reaction mixture was filtered through a pad of Celite
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was re-dissolved in hot H2O
  4. filtrationthe resulting suspension filtered through a pad of Celite
  5. customSolvent was removed under reduced pressure
  6. dry with materialthe residue dried via three MeOH-azeotrope cycles
  7. customThe resulting residue was reprecipitated

出典と根拠

ORDレコード
ord-f122677273e246f69f73d69bb814cb1f
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07790746B2

反応ノート

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