Hydrochloric Acid → HCID 13935011, compound

HRID 2308907Notes

Reaction equation

HRID 2308907 reaction equation
Cl.[NH2:2][C:3]1[C:4]([Cl:18])=[C:5]([CH2:9][N:10]2[C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[CH2:12][O:11]2)[CH:6]=[CH:7][CH:8]=1.N([O-])=O.[Na+].[N-:23]=[N+:24]=[N-].[Na+]>O>[N:2]([C:3]1[C:4]([Cl:18])=[C:5]([CH2:9][N:10]2[C:14](=[O:15])[C:13]([CH3:16])([CH3:17])[CH2:12][O:11]2)[CH:6]=[CH:7][CH:8]=1)=[N+:23]=[N-:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 20186297HCID 20186297, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13935011HCID 13935011, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

Concentrated hydrochloric acid (25 ml) was added dropwise to a stirred mixture of 2-[(3-amino-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (6.45 g, 0.025 mole) and water (75 ml). The reaction mixture was cooled to 0° C., and a solution of sodium nitrite (2.0 g, 0.03 moles) in water (25 ml) was added dropwise. Upon completion of addition, the reaction mixture was stirred at 0° C. for 30 minutes. An insoluble material was removed by filtration. The filtrate was cooled to 0° C., and sodium azide (1.6 g, 0.025 mole) was added portionwise. Upon completion of addition, the reaction mixture was stirred for 15 minutes. The reaction mixture was diluted with water (500 ml) and extracted with methylene chloride (3×100 ml). The dried (sodium sulfate) methylene chloride extract was concentrated under reduced pressure to yield 5.3 g of 2-[(3-azido-2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone as a brown oil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. customAn insoluble material was removed by filtration
  3. temperatureThe filtrate was cooled to 0° C.
  4. additionUpon completion of addition
  5. stirringthe reaction mixture was stirred for 15 minutes
  6. extractionextracted with methylene chloride (3×100 ml)
  7. dry with materialThe dried (sodium sulfate) methylene chloride
  8. extractionextract
  9. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-ecfdba6d780948c8b2152968539affd3
Source dataset
uspto-grants-1987_09
Patent number
US04692182

Reaction notes

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