Acetic Acid → LY-367366

HRID 442805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442805
C([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:16][CH:17]3[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:24][C:23]4[C:18]3=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:13]C(=O)N[C:10]2=[O:15])=[CH:5][CH:4]=1)#N.[C:31]([OH:34])(=[O:33])C.[OH-:35].[Na+]>>[NH2:13][C:9]([C:6]1[CH:5]=[CH:4][C:3]([C:31]([OH:34])=[O:33])=[CH:8][CH:7]=1)([CH2:16][CH:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=2[S:24][C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:10]([OH:15])=[O:35]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 14798Sodium Hydroxide2×HCID 536856165-(4-Cyanophenyl)-5-(9H-thioxanthen-9-ylmethyl)hydantoin

Produkt 1

HCID 9844204LY-367366

Versuchsvorschrift

5-(4-Cyanophenyl)-5-(9H-thioxanthen-9-ylmethyl)hydantoin (2.3 g, 5.5 mmol) was hydrolysed in aqueous sodium hydroxide (16.5 ml) following the procedure described in Example 1 (vi) for 72 h at 150° C. The cooled reaction mixture was then acidified with acetic acid, the resulting solid precipitate was filtered and washed with diethylether to give an off white solid. The solid was redissolved in aqueous sodium hydroxide (2M), filtered through a celite pad and acidified with acetic acid, filtered, washed with water, diethylether and finally methanol and then dried in vacuo to give the title compound as a white solid, m.p. 251° C.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. filtrationthe resulting solid precipitate was filtered
  3. washwashed with diethylether
  4. customto give an off white solid
  5. filtrationfiltered through a celite pad
  6. filtrationfiltered
  7. washwashed with water, diethylether and finally methanol
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-848633011134443fb2f428350cdf227a
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891899

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