Amidinothiourea → 4-(6-(Acetamidomethyl)pyridin-2-yl)-2-guanidinothiazole

HRID 2379847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2379847
[C:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=O)[CH2:13]Br)[N:7]=1)(=[O:3])[CH3:2].[NH2:16][C:17](=[N:19][C:20]([NH2:22])=[S:21])[NH2:18]>C(O)C>[C:1]([NH:4][CH2:5][C:6]1[N:7]=[C:8]([C:12]2[N:22]=[C:20]([N:19]=[C:17]([NH2:18])[NH2:16])[S:21][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 2724563AmidinothioureaHCID 10445869Acetamide, N-[[6-(bromoacetyl)-2-pyridinyl]methyl]-

Produkt 1

HCID 104469404-(6-(Acetamidomethyl)pyridin-2-yl)-2-guanidinothiazoleAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(acetylaminomethyl)-6-bromoacetylpyridine (50.0 g) and diaminomethylenethiourea (15.3 g) in ethanol (400 ml) was stirred at 40° to 50° C. for 2 hours. The solvent was removed by concentration in vacuo. To the residue was added a mixture of water, ethyl acetate and tetrahydrofuran, and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (85:15, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was triturated with a mixture of ethyl acetate and diisopropyl ether to give 4-(6-acetylaminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (18.73 g).

Aufarbeitung

  1. customThe solvent was removed by concentration in vacuo
  2. additionTo the residue was added
  3. additiona mixture of water, ethyl acetate and tetrahydrofuran
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. customwas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (85:15, V/V)
  9. additionThe eluted fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo
  12. customThe residue was triturated with a mixture of ethyl acetate and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e94f89df1a9e443e90a93bef6b554702
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05364871

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