Methanol → 2-Amino-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667676
[N:1]([C:4]1[S:5][C:6]([C:19]([NH2:21])=[O:20])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:8]=1)=[N+]=[N-].CO.[Cl-].[NH4+]>[Zn].O1CCCC1>[NH2:1][C:4]1[S:5][C:6]([C:19]([NH2:21])=[O:20])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)[N:8]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 866428032-Azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

Produkt 1

HCID 593753582-Amino-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amideAusbeute 102,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.9035 g (2.884 mmole) of 2-azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide, 27 mL of methanol and 27 mL of tetrahydrofuran, was added 1.91 g (29.21 mg-atom) of zinc and 3.82 g (71.42 mmole) of ammonium chloride. The mixture was stirred vigorously for 1 hour, and then filtered through Diatomaceous earth, washing the filter pad with methanol and tetrahydrofuran. The filtrate was concentrated under reduced pressure, diluted with 350 mL of ethyl acetate and washed three times with 100 mL of water, twice with 50 mL of brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to give 0.8527 g of 2-amino-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (V.48).

Aufarbeitung

  1. filtrationfiltered through Diatomaceous earth
  2. washwashing the filter pad with methanol and tetrahydrofuran
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additiondiluted with 350 mL of ethyl acetate
  5. washwashed three times with 100 mL of water
  6. dry with materialtwice with 50 mL of brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6dffa36a72d143c69565c2b5d0361da7
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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