Hydrochloric Acid → HCID 70193605, compound

HRID 1608988Notes

Reaction equation

HRID 1608988 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 23668193Sodium NitriteHCID 70195982(4R)-4-[(4-AMinophenyl)Methyl]-2-oxazolidinone Monohydrochloride

Product 1

HCID 70193605HCID 70193605, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

The product from step (b) (10.3 g) was suspended in water (53 ml) and c.HCl (106 ml) added dropwise. The resulting mixture was cooled to -5° C. and a solution of sodium nitrite (3.2 g) in water (30 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 (51 g) in c.HCl (91 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 (11 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-5f7a55250ec1465e9d1dac77dfd6b3a7
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

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