Propane sultone → HCID 87456726, compound

HRID 1591537Notes

Reaction equation

HRID 1591537 reaction equation
[CH3:1][CH:2]1[N:6]=[C:5]2[CH:7]=[CH:8][N:9]=[C:4]2[S:3]1.[CH2:10]1[CH2:16][S:13](=[O:15])(=[O:14])[O:12][CH2:11]1>>[CH3:1][CH:2]1[N+:6]([CH2:11][CH2:10][CH2:16][S:13]([O-:15])(=[O:14])=[O:12])=[C:5]2[CH:7]=[CH:8][N:9]=[C:4]2[S:3]1

Participants

3

Reactant 2

HCID 14264Propane sultoneHCID 68446104HCID 68446104, compound

Product 1

HCID 87456726HCID 87456726, compoundYield 92.2%

Conditions

Temperature
130 °C

Procedure

2-Methylpyrrolo[3,2-d]thiazole (0.70 g) (5mmol) and 0.67 g of 1,3-propanesultone (5.5 mmol) were stirred with heating at 130° C. for 6 hours. After cooling, the crystals precipitated were filtered out and washed with acetone, thereby 1.2 g of 3-[2-methyl-1-pyrrolo[3,2-d]thiazolio]propanesulfonate was obtained (yield: 92%). 3-[5- Chloro-2-(3-sulfopropyl)thio-1-benzothiazolio]propanesulfonate (0.45 g) (1 mmol), 2 ml of dimethyl sulfoxide and 2 ml of acetonitrile were added to 0.26 g of the quaternary salt of 3-[2-methyl-1-pyrrolo[3,2-d]thiazolio]propanesulfonate (1 rmmol) and the mixture was stirred at 50° C. with adding 0.56 ml of triethylamine (4 mmol), followed by further stirring for 1 hour. The solution was concentrated, and then refined with column chromatography, thereby 0.10 g of the objective Methine Dye S-125 was obtained. Yield: 15%, ?max (MeOH)=447.5 nm.

Workup

  1. temperatureAfter cooling
  2. customthe crystals precipitated
  3. filtrationwere filtered out
  4. washwashed with acetone

Sources & evidence

ORD record
ord-6785add4725844b3b705d67696c18362
Source dataset
uspto-grants-2007_11
Patent number
US07291449B2

Reaction notes

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