Methyl thiophene-2-carbimidothioate hydroiodide → HCID 178465426, Verbindung

HRID 1668500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668500
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:16][CH2:15][CH:14]([N:17]([CH2:25][CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH:12]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.I.CS[C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[NH:31]>CCO>[CH2:25]([N:17]([CH:14]1[CH2:15][CH2:16][C:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([NH:1][C:30]([C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)=[NH:31])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)=[CH:12][CH2:13]1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH3:26]

Komponenten

4

Edukt 2

HCID 66704664Methyl thiophene-2-carbimidothioate hydroiodideHCID 68254813HCID 68254813, Verbindung

Produkt 1

HCID 178465426HCID 178465426, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of above compound 130 in dry EtOH (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.29 g, 1.037 mmol) at room temperature and stirred for 24 h. Solvent was evaporated and crude was diluted with sat. NaHCO3 solution (20 mL) and product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layer washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 131 (0.18 g, 75%, over two steps) as a yellow solid. mp 110-112° C.; 1H NMR (DMSO-d6) δ 1.09 (t, 3H, J=6.6 Hz), 1.42 (s, 9H), 1.82-1.93 (m, 2H), 2.22-2.64 (m, 4H), 3.12-3.18 (m, 2H), 4.06 (brs, 1H), 6.10 (s, 1H), 6.32 (s, 2H), 6.60 (d, 1H, J=8.4 Hz), 6.82 (s, 1H), 7.09 (t, 1H, J=4.5 Hz), 7.23 (s, 1H), 7.59 (d, 1H, J=4.8 Hz), 7.68-7.73 (m, 2H), 10.84 (s, 1H); ESI-MS (m/z, %) 465 (MH+, 100).

Aufarbeitung

  1. customSolvent was evaporated
  2. additioncrude was diluted with sat. NaHCO3 solution (20 mL) and product
  3. extractionwas extracted into CH2Cl2 (2×20 mL)
  4. washThe combined CH2Cl2 layer washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-dba117014ab04677938ff64bc93ca59c
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989447B2

Notizen zur Reaktion

Wird geladen…