Pyridine → HCID 15225531, compound

HRID 1492909Notes

Reaction equation

HRID 1492909 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[CH2:17]([O:19][P:20]([CH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([O:22][CH2:23][CH3:24])=[O:21])[CH3:18]>ClCCl.C(=O)([O-])O.[Na+]>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:1][C:30]([C:29]1[CH:33]=[CH:34][C:26]([CH2:25][P:20](=[O:21])([O:19][CH2:17][CH3:18])[O:22][CH2:23][CH3:24])=[CH:27][CH:28]=1)=[O:31]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8706Benzo(d)thiazol-2-amineHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chloride

Product 1

HCID 15225531HCID 15225531, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

In 30 ml of dry dichloromethane were dissolved 3.0 g of 2-aminobenzothiazole and 10 ml of pyridine and while the resulting solution was stirred under ice-cooling, a solution of 5.8 g 4-[(diethoxyphosphoryl)methyl]benzoyl chloride in 10 ml dry dichloromethane was slowly added dropwise. The stirring was continued at room temperature for 10 hours, after which the reaction mixture was diluted with 30 ml of 10% aqueous sodium hydrogen carbonate solution and extracted with chloroform. The chloroform layer was washed serially with 30 ml of 10% hydrochloric acid and 30 ml of water and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: chloroform-ethyl acetate=1:1) and the resulting crude crystals were recrystallized from ethanol to provide 6.8 g of the title compound as colorless crystals. The structure and melting point of the compound thus obtained are shown in Table 1.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed serially with 30 ml of 10% hydrochloric acid and 30 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-b5cd6309e3514d81bee6fd713ab72da0
Source dataset
uspto-grants-1994_12
Patent number
US05376665

Reaction notes

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