Ammonia → 4-[2-(Cyclopropylamino)-1,3-thiazol-4-yl]benzoic acid

HRID 606609

Reaktionsgleichung

Reaktionsgleichung von HRID 606609
N(C1CC1)=C=S.N.[CH:8]1([NH:11][C:12]([NH2:14])=[S:13])[CH2:10][CH2:9]1.Br[CH2:16][C:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)=O>C1COCC1.CO>[CH:8]1([NH:11][C:12]2[S:13][CH:16]=[C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)[N:14]=2)[CH2:10][CH2:9]1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 92463Cyclopropyl isothiocyanateHCID 2560481CyclopropylthioureaHCID 27568364-(2-bromoacetyl)benzoic Acid

Produkt 1

HCID 598073364-[2-(Cyclopropylamino)-1,3-thiazol-4-yl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Isothiocyanato-cyclopropane (4 g) was mixed with ammonia (37% in water, 8 mL) and methanol (32 mL) at 0° C. and then stirred for 16 hours at room temperature. The mixture was then cooled to 0° C., filtered, washed with a little water and dried. The Cyclopropyl-thiourea (2.06 mmol) and 4-(2-Bromo-acetyl)-benzoic acid (2.06 mmol) were mixed in THF (12 mL). After stirring at room temperature for 5 minutes the mixture was heated to 80° C. for 2 hours. The mixture was then cooled to room temperature and filtered. The solid was washed with a small amount of diethylether and dried. m/z=261.0 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification.

Aufarbeitung

  1. temperatureThe mixture was then cooled to 0° C.
  2. filtrationfiltered
  3. washwashed with a little water
  4. customdried
  5. stirringAfter stirring at room temperature for 5 minutes the mixture
  6. temperaturewas heated to 80° C. for 2 hours
  7. temperatureThe mixture was then cooled to room temperature
  8. filtrationfiltered
  9. washThe solid was washed with a small amount of diethylether
  10. customdried
  11. customused in the next step without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-c67c9cd284d44601a1600ebb9725d42c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915300B2

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