Methanol → HCID 86750599, compound

HRID 977235Notes

Reaction equation

HRID 977235 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1)=O.Cl.[NH2:34][OH:35].C([O-])(=O)C.[Na+].CO>O>[OH:35][N:34]=[C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1)[CH2:14][CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10961013HCID 10961013, compound

Product 1

HCID 86750599HCID 86750599, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propyl]-2,4-oxazolidinedione (0.28 g), hydroxylamine hydrochloride (0.09 g), sodium acetate (0.11 g) and 80% methanol (20 ml) was stirred under refluxing conditions for 2 hours. The reaction mixture was poured over water; the resulting crystal was collected by filtration to yield 5-[3-[4-[1-hydroxyimino-3-(5-methyl-2-phenyl-4-oxazolyl)propyl]phenyl]propyl]-2,4-oxazolidinedione (0.26 g, 90%), which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 185°-186° C.

Workup

  1. filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-adb8bb4e684b4182bdb310c6397fa1ff
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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