Sodium Hydroxide → HCID 20222819, compound

HRID 979790Notes

Reaction equation

HRID 979790 reaction equation
[SH:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].Cl[CH2:14][CH2:15][CH2:16][NH2:17]>C(O)C.O>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:14][CH2:15][CH2:16][NH2:17]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 846293-ChloropropylamineHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 20222819HCID 20222819, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

2-Mercaptobenzoxazole (15.2 g; 0.1 mol) was dissolved in ethanol (200 ml); NaOH (4.0 g; 0.1 mol) dissolved in water was added thereto. The reaction mixture was refluxed for 30 minutes, then 3-chloropropylamine (9.3 g; 0.1 mol) dissolved in ethanol (50 ml) was added. The mixture was refluxed for 90 minutes, cooled, filtered from the salt and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol/ether (1:3), (15.0 g; 71.6% yield).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 30 minutes
  3. additionwas added
  4. temperatureThe mixture was refluxed for 90 minutes
  5. temperaturecooled
  6. filtrationfiltered from the salt
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with methanol/ether (1:3), (15.0 g; 71.6% yield)

Sources & evidence

ORD record
ord-38f227947a06414c9d6dbf421925fae7
Source dataset
uspto-grants-1987_01
Patent number
US04634701

Reaction notes

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