Isopropanol → Etamicastat

HRID 1693640Notes

Reaction equation

HRID 1693640 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[N:9]([C@@H:10]2[CH2:19][C:18]3[C:13](=[C:14]([F:21])[CH:15]=[C:16]([F:20])[CH:17]=3)[O:12][CH2:11]2)[C:8](=[S:22])[NH:7][CH:6]=1.CC(O)C.ClCCl.[OH-].[Na+]>O>[NH2:2][CH2:3][CH2:4][C:5]1[N:9]([C@@H:10]2[CH2:19][C:18]3[C:13](=[C:14]([F:21])[CH:15]=[C:16]([F:20])[CH:17]=3)[O:12][CH2:11]2)[C:8](=[S:22])[NH:7][CH:6]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10450386Etamicastat HCl salt

Product 1

HCID 10450387Etamicastat

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
36.5 °C

Procedure

(R)-5-(2-Aminoethyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione hydrochloride (9.64 g, 27.72 mmol) was dissolved in water (160 ml) at 40-45° C. with stirring. To the resulting solution 2-propanol (64 ml) was added, the mixture was cooled to 35-38° C., dichloromethane (256 ml) was added followed by 1N NaOH (28 ml, 28 mmol) and the stirring continued for 10-15 min. Lower organic phase was separated, dried over MgSO4 and evaporated under reduced pressure to approx. 40 ml. The resulting suspension was diluted with petroleum ether (200 ml), the precipitate was collected, was with petroleum ether on the filter, dried in vacuum. Yield 7.8 g (91%), mp 192-5° C. (dec).

Workup

  1. customLower organic phase was separated
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure to approx. 40 ml
  4. additionThe resulting suspension was diluted with petroleum ether (200 ml)
  5. customthe precipitate was collected
  6. customdried in vacuum

Sources & evidence

ORD record
ord-7517237506db4d099ccbdc28bf297350
Source dataset
uspto-grants-2012_04
Patent number
US08158666B2

Reaction notes

Loading…