Acetic Acid → LY-367366

HRID 442805Notes

Reaction equation

HRID 442805 reaction equation
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]

Participants

4

Reactant 3

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

Product 1

HCID 9844204LY-367366

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-848633011134443fb2f428350cdf227a
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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