Sodium hydride → HCID 21999695, compound

HRID 1975883Notes

Reaction equation

HRID 1975883 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][Cl:24]>O1CCCC1>[Cl:24][CH2:23][CH2:22][CH2:21][CH2:20][N:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutaneHCID 230981Anilinobenzothiazole

Product 1

HCID 21999695HCID 21999695, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.05 mol) was added portionwise to a solution of N-phenyl-2-benzothiazolamine, prepared according to the procedure described in J. Chem. Soc, 1962, 230, (0.05 mol) in tetrahydrofuran (200 ml). The mixture was stirred for 15 minutes. A solution of 1-bromo-4-chlorobutane (0.05 mol) in tetrahydrofuran (50 ml) was added dropwise and the resulting reaction mixture was stirred and refluxed for 48 hours. The mixture was cooled, and the solvent was evaporated. The residue was partitioned between water and CH2Cl2. The organic layer was separated, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2). The desired fractions were collected and the solvent was evaporated, yielding 10.4 g (66%) of N-(4-chlorobutyl)-N-phenyl-2-benzothiazolamine (interm. 10). N-(5-chloropentyl)-N-phenyl-2-benzothiazolamine (interm. 24) was prepared similarly.

Workup

  1. customprepared
  2. customthe resulting reaction mixture
  3. stirringwas stirred
  4. temperaturerefluxed for 48 hours
  5. temperatureThe mixture was cooled
  6. customthe solvent was evaporated
  7. customThe residue was partitioned between water and CH2Cl2
  8. customThe organic layer was separated
  9. customdried
  10. filtrationfiltered
  11. customthe solvent evaporated
  12. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
  13. customThe desired fractions were collected
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-eb34a648e6ee43729c32e486d4c7a2c7
Source dataset
uspto-grants-2001_05
Patent number
US06224849B1

Reaction notes

Loading…