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1,2-Dichloroethane → HCID 66685531, compound

HRID 922248
Notes
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Reaction equation

HRID 922248 reaction equation
ClCCCl.[CH3:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[O:8][N:7]=1.[I:20]N1C(=O)CCC1=O.OS(O)(=O)=O>O>[I:20][C:10]1[C:6]([CH3:5])=[N:7][O:8][C:9]=1[C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 37721263-Methyl-5-(4-nitrophenyl)isoxazole

Product 1

HCID 66685531HCID 66685531, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a 100 mL RB flask fitted with magnetic stirrer was charged with 10 mL of 1,2-dichloroethane. To the stirring solution were added 3-methyl-5-(4-nitrophenyl)-1,2-oxazole (0.27 g, 1.30 mmol), N-iodosuccinimide (0.28 g, 1.24 mmol), followed by concentrated H2SO4 (0.2 mL) at 0° C. and stirred at room temperature for 4 h. The reaction mixture was poured into water (30 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with sodium thiosulphate solution (30 mL), water (30 mL) and saturated brine solution (10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as yellow solid (0.40 g, yield: 93.7%). 1H NMR (300 MHz, CDCl3): δ 8.29-8.32 (dd, 2H), 8.18-8.21 (dd, 2H), 2.33 (s, 3H).

Workup

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with sodium thiosulphate solution (30 mL), water (30 mL) and saturated brine solution (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fda15d37112f4d62a8fe5323a8e6e953
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278915B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes