Ammonium Hydroxide → 5-Bromo-2-methyl-thiazole-4-carboxylic acid amide

HRID 1443108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443108
[Br:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([OH:10])=O.C1N=C[N:13](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>CN(C=O)C>[Br:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([NH2:13])=[O:10]

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 451175845-Bromo-2-methyl-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 685440505-Bromo-2-methyl-thiazole-4-carboxylic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5-Bromo-2-methyl-thiazole-4-carboxylic acid (14.4 g, 64.8 mmol) was dissolved in 100 ml DMF and CDI (11.6 g, 71.3 mmol) was added. The solution was stirred for 2 hrs at 60° C., cooled and NH4OH (150 ml, 973 mmol) was added. The reaction mixture was stirred over night at room temperature and extracted two times with ethyl acetate and water. The organic extracts were washed four times with water, dried with sodium sulfate, filtered and evaporated. The crude product (11.3 g, 79%) [MS: m/e=222.8 (M+H+)] was used without any further purification for the next step.

Aufarbeitung

  1. temperaturecooled
  2. stirringThe reaction mixture was stirred over night at room temperature
  3. extractionextracted two times with ethyl acetate and water
  4. washThe organic extracts were washed four times with water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product (11.3 g, 79%) [MS: m/e=222.8 (M+H+)] was used without any further purification for the next step

Quellen und Nachweise

ORD-Eintrag
ord-bc0ec2d5171a4ebcb94a3a722b7cae87
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659401B2

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