Sulfuric Acid → HCID 23371895, compound

HRID 1900074Notes

Reaction equation

HRID 1900074 reaction equation
N[C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]2=[O:22])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.S(=O)(=O)(O)[OH:24].N([O-])=O.[Na+]>O>[CH:8]1([C:7]2[CH:6]=[CH:5][C:4]([N:14]3[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]3=[O:22])=[CH:3][C:2]=2[OH:24])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23371851HCID 23371851, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23371895HCID 23371895, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

200 mg (0.7 mmol) of (RS)-3-(3-amino-4-cyclohexyl-phenyl)-5-methoxymethyl-oxazolidin-2-one were suspended in a mixture of 0.86 ml of water, 0.72 g of ice and 0.235 ml of conc. sulfuric acid and treated at 0°-50 with a solution of 45 mg (0.66 mmol) of sodium nitrite in 0.4 ml of water. After boiling under reflux for 3 hours the mixture was extracted with dichloromethane, dried with sodium sulfate and the solvent was distilled off. Chromatography over silica gel with ethyl acetate/hexane 1:2 gave 120 mg (60%) of white crystals with m.p. 207°-208°.

Workup

  1. temperatureunder reflux for 3 hours the mixture
  2. extractionwas extracted with dichloromethane
  3. dry with materialdried with sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-792bd87e71d04bfdbebee3700273881f
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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