Ethyl Acetate → Lorazepam

HRID 1700799

Reaction equation

HRID 1700799 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([Cl:21])=[C:5]([C:7]2[C:14]3[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=3[NH:12][C:10](=[O:11])[CH:9]([OH:20])[N:8]=2)[CH:6]=1.C(O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:1]1[CH:2]=[CH:3][C:4]([Cl:21])=[C:5]([C:7]2[C:14]3[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=3[NH:12][C:10](=[O:11])[CH:9]([OH:20])[N:8]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 18318790HCID 18318790, compound

Product 1

HCID 3958LorazepamYield 94.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Lorazepam ethanol solvate (100 g) was suspended in a 1:1 mixture of ethyl acetate and toluene (400 ml). The suspension was heated to 60° C. for 1 hour with rapid stirring and then cooled to 15° C. The suspension was filtered to recover the lorazepam. The lorazepam crystals were then washed with ethyl acetate (20 ml) and dried under 65 mm Hg vacuum at about 50° C. for about two hours to give crystalline lorazepam (83 g) in 88% yield.

Workup

  1. temperaturecooled to 15° C
  2. filtrationThe suspension was filtered
  3. customto recover the lorazepam
  4. washThe lorazepam crystals were then washed with ethyl acetate (20 ml)
  5. customdried under 65 mm Hg vacuum at about 50° C. for about two hours

Sources & evidence

ORD record
ord-639a7eb95e2a4bee901453557bc86718
Source dataset
uspto-grants-2002_02
Patent number
US06350870B2

Linked notes

Loading…