Hydrochloric Acid → HCID 23371865, compound

HRID 1900073Notes

Reaction equation

HRID 1900073 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.Cl.N([O-])=O.[Na+].[I-:28].[K+]>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[I:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 23371851HCID 23371851, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 23371865HCID 23371865, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

180 mg (0.6 mmol) of (RS)-3-(3-amino-4-cyclohexyl-phenyl)-5-methoxymethyl-oxazolidin-2-one (from the mother liquor of the foregoing reaction) were suspended in a mixture of 0.32 ml of water, 0.32 g of 37 percent hydrochloric acid and 0.64 g of ice and treated with a solution of 41.4 mg (0.6 mmol) of sodium nitrite in 0.3 ml of water at 0°-5°. After stirring at this temperature for 30 minutes a solution of 0.1 g (0.6 mmol) of potassium iodide in 0.3 ml of water was added. The mixture was stirred at room temperature overnight, extracted with ethyl acetate and chromatographed over silica gel with ethyl acetate/hexane 3:1 to give 100 mg of oil. MS: m/e (% basic peak): 415 (M+, 100), 372 (5), 346 (9), 289 (9), 245 (12), 143 (15), 71 (22).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. customchromatographed over silica gel with ethyl acetate/hexane 3:1

Sources & evidence

ORD record
ord-3b0d200bf96249b1bdea72f557461bd7
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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