Tetrahydrofuran → HCID 87732812, compound

HRID 746327Notes

Reaction equation

HRID 746327 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.[CH2:17]1[CH2:23][S:20](=[O:22])(=[O:21])[O:19][CH2:18]1.O1CCCC1>CN1CCCC1=O>[CH3:1][N:2]([CH3:16])[C:3]1[CH:4]=[CH:5][C:6]([N:9]=[N:10][C:11]2[S:12][CH:13]=[CH:14][N+:15]=2[CH2:18][CH2:17][CH2:23][S:20]([O-:22])(=[O:21])=[O:19])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14264Propane sultoneHCID 29844463019-44-3

Product 1

HCID 87732812HCID 87732812, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

0.5 g (1.5 mmol) of N,N-dimethyl-4-[1,3-thiazol-2-yldiazenyl]aniline are dissolved in 1-methyl-2-pyrrolidinone (NMP), and 0.9 g (7.5 mmol) of 1,3-propane sultone is added. The reaction mixture is heated at, 100° C. for 4 hours. After cooling, 20 ml of tetrahydrofuran are added to the reaction mixture and the precipitated product is filtered off, washed with acetone and dried. The resulting dye is recrystallized from methanol/ethyl acetate. 0.53 g (45% of theory) of 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate is obtained as a dark blue powder.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated product is filtered off
  3. washwashed with acetone
  4. customdried
  5. customThe resulting dye is recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-f859aa1b0d164cf7b4becbdc9bee7951
Source dataset
uspto-grants-2008_07
Patent number
US07393366B2

Reaction notes

Loading…