Propane sultone → HCID 86707260, compound

HRID 630590Notes

Reaction equation

HRID 630590 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[C:11]3[CH:15]=[CH:14][S:13][C:12]=13)[N+:9](CCCS([O-])(=O)=O)=[C:8]([CH3:23])[C:7]2([CH3:25])[CH3:24])([OH:3])=[O:2].C1CS(=O)(=O)OC1.[OH-].[Na+]>S1(CCCC1)(=O)=O.Cl>[CH3:23][C:8]1[C:7]([CH3:24])([CH3:25])[C:6]2[C:10](=[C:11]3[CH:15]=[CH:14][S:13][C:12]3=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[N:9]=1

Participants

6

Reactant 3

HCID 14264Propane sultoneHCID 14798Sodium HydroxideHCID 86707261HCID 86707261, compound

Product 1

HCID 86707260HCID 86707260, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
25 °C

Procedure

Synthesis of 5-carboxy-2,3,3-trimethyl-1-(3-sulfonatopropyl)-3H-thieno[2,3-g]indol-1-ium BE: A solution of BD (210 mg, 0.81 mmole) and 1,3-propanesultone (530 mg, 4.3 mmole) in 0.4 mL sulfolane was heated at 180° C. for 1 hr and cooled down to 25° C. The reaction was diluted with 0.5 mL 6 N HCl and heated to 80° C. for 1 hr and cooled down to to 25° C. The solution was neutralized with 2N NaOH solution to pH 9. The product was purified by reverse phase HPLC eluted with a gradient of CH3CN over 0.1 N TEAB buffer. The yield of the desired product BE was 172 mg (44%).

Workup

  1. temperatureheated to 80° C. for 1 hr
  2. temperaturecooled down to to 25° C
  3. customThe product was purified by reverse phase HPLC
  4. washeluted with a gradient of CH3CN over 0.1 N TEAB buffer

Sources & evidence

ORD record
ord-cdcaedc1f5f14405bcaf866c1b5fe396
Source dataset
uspto-grants-2016_04
Patent number
US09315864B2

Reaction notes

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