Hydrochloric Acid → (S)-4-(4-Hydrazinylbenzyl)oxazolidin-2-one hydrochloride

HRID 128963Notes

Reaction equation

HRID 128963 reaction equation
Cl.[NH2:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)=[CH:5][CH:4]=1.Cl.[N:17]([O-])=O.[Na+].[Sn](Cl)[Cl:22]>O>[ClH:22].[NH:2]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)=[CH:5][CH:4]=1)[NH2:17]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 24479Stannous ChlorideHCID 11543152(S)-4-(4-Aminobenzyl)-1,3-oxazolidin-2-one hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 45356867(S)-4-(4-Hydrazinylbenzyl)oxazolidin-2-one hydrochlorideYield 114%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

The product from step (d) (0.79 g) was suspended in water (4.8 ml) and c.HCl (8.1 ml) added dropwise. The resulting mixture was cooled to -5° C. and a solution of sodium nitrite (0.24 g) in water (2.4 ml) added dropwise to the stirred mixture over 15 minutes followed by 30 minutes' stirring at -5° to 0° C. The solution was then added at 0° C. over 15 minutes to a stirred solution of tin (II) chloride (3.8 g) in c.HCl (6.9 ml), followed by 3 hours' stirring at room temperature. The solution was evaporated in vacuo and the residue triturated with ether to give the desired product as a pale yellow solid (0.96 g).

Workup

  1. stirring' stirring at room temperature
  2. customThe solution was evaporated in vacuo
  3. customthe residue triturated with ether

Sources & evidence

ORD record
ord-1e11ad6f41f64963b3c1219e34c98c37
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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