Chlorosuccinimide → HCID 59796835, compound

HRID 33575Notes

Reaction equation

HRID 33575 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:17])[O:5][C:6]=1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[Cl:18]N1C(=O)CCC1=O>ClCCl>[Cl:18][CH2:1][C:2]1[N:3]=[C:4]([NH2:17])[O:5][C:6]=1[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 112761502-Amino-4-methyl-5-(naphth-1-yl)oxazole

Product 1

HCID 59796835HCID 59796835, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-methyl-5-naphthalen-1-yl-oxazol-2-ylamine (3, 800 mg), N-chlorosuccinimide (480 mg) and dichloromethane (30 mL) were irradiated with a 150W (tungsten/halogen) lamp at reflux for 8 hours. After cooling to room temperature, the solution was diluted with dichloromethane (50 mL) and washed with a saturated solution of sodium hydrogen carbonate (50 mL), water (50 mL) and brine (50 mL). The solvent was removed under reduced pressure and the resultant residue was purified by column chromatography affording 4-chloromethyl-5-naphthalen-1-yl-oxazol-2-ylamine (27) (411 mg, 45%) as an orange foam, 1H NMR (DMSO-D6): 4.45 (2H, s), 6.95 (2H, br s), 7.5-7.6 (4H, m), 7.95-8.00 (3H, m).

Workup

  1. temperatureat reflux for 8 hours
  2. washwashed with a saturated solution of sodium hydrogen carbonate (50 mL), water (50 mL) and brine (50 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-aaebab399bbc4db6bcad2931a351399f
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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