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1,1'-Carbonyldiimidazole → {2-[(5-Diallylaminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

HRID 11568
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11568
[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:29]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH2:43])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1COCC1>[C:32]([O:31][C:29](=[O:30])[NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][C:14]([C:12]1[S:13][C:9]([CH2:8][N:4]([CH2:1][CH:2]=[CH2:3])[CH2:5][CH:6]=[CH2:7])=[CH:10][CH:11]=1)=[O:16])([CH3:35])([CH3:33])[CH3:34]
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Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 219759135-Diallylaminomethyl-thiophene-2-carboxylic acid

Produkt 1

HCID 69655347{2-[(5-Diallylaminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl esterAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 2.70 g (11.38 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid in 50 ml THF was added 2.03 g (12.51 mmol) carbonyldiimidazol. After 45 min at rt, 2.48 g (11.95 mmol) mono-boc-ortho-phenylenediamine were added to the reaction mixture, and it was stirred for 3 h at rt. The solvent was evaporated and the residue dissolved in ethyl acetate. The organic phase was washed twice with sat. NaHCO3, once with water and dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/heptane 2:8) to yield 4.10 g (9.59 mmol) {2-[(5-Diallylaminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; exact MW [M+H] calc'd: 428.20; MW found [M+H]: 428.3.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic phase was washed twice with sat. NaHCO3, once with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b8e9914bc2ed46f08901e363f3b422c0
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07098247B2

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