2-Chlorobenzothiazole → HCID 21999700, compound

HRID 1975881Notes

Reaction equation

HRID 1975881 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].Cl[C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.[I-]>CC(CC(C)C)=O.C(=O)([O-])[O-].[Na+].[Na+]>[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 30165Iodide IonHCID 110078755-(methylamino)pentanol

Product 1

HCID 21999700HCID 21999700, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5-(methylamino)pentanol (0.23 mol), 2-chlorobenzothiazole (0.3 mol), sodium carbonate (0.4 g) and potssium iodide (catalytic quantity) in methylisobutyl-keton (1000 ml) was stirred and refluxed overnight. The reaction mixture was cooled, washed with water, dried, filtered and the filtrate was evaporated. The residue was stirred in water, acidified with HCl, stirred, washed with diisopropylether, and the acidic layer was alkalized with NH4OH. This mixture was extracted twice with CH2Cl2. The separated organic layer was dried, filtered, and the solvent was evaporated, yielding 56 g of N-(5-hydroxypentyl)-N-methyl-2-benzothiazolamine (interm. 7).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. stirringThe residue was stirred in water
  8. stirringstirred
  9. washwashed with diisopropylether
  10. extractionThis mixture was extracted twice with CH2Cl2
  11. customThe separated organic layer was dried
  12. filtrationfiltered
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3727b1a38be9460cabe0939401a086b6
Source dataset
uspto-grants-2001_05
Patent number
US06224849B1

Reaction notes

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