Chlorosulfonic acid → HCID 178464495, compound

HRID 1012042Notes

Reaction equation

HRID 1012042 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](/[N:19]=[N:20]/[C:21]2[CH:26]=[CH:25][C:24]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][OH:30])=[CH:23][CH:22]=2)[S:5][C:6]=1[CH:7]=[C:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].Cl[S:34]([OH:37])(=[O:36])=[O:35]>C1COCC1>[S:34]([OH:37])([O:30][CH2:29][CH2:28][N:27]([C:24]1[CH:23]=[CH:22][C:21](/[N:20]=[N:19]/[C:4]2[S:5][C:6]([CH:7]=[C:8]3[C:9](=[O:18])[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:16]3=[O:17])=[C:2]([Cl:1])[N:3]=2)=[CH:26][CH:25]=1)[CH2:31][CH3:32])(=[O:36])=[O:35]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178464434HCID 178464434, compound

Product 1

HCID 178464495HCID 178464495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.5 g (1.07 mmol) 2-{[4-chloro-2-((E)-{4-[ethyl(2-hydroxyethyl)amino]-phenyl}-diazenyl)-1,3-thiazol-5-yl]methylidene}-1H-indene-1,3(2H)-dione were dissolved in 50 ml THF and cooled to 0° C. Then 0.19 g (1.60 mmol) chlorosulfonic acid were added slowly drop by drop with stirring. After the addition was completed, the reaction mixture was heated under reflux for 4 hours, allowed to cool to room temperature and stirred overnight. After further cooling in an ice bath the formed precipitate was filtered off, washed with a little cold THF and dried at 40° C. in vacuum.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 4 hours
  4. temperatureto cool to room temperature
  5. stirringstirred overnight
  6. temperatureAfter further cooling in an ice bath the formed precipitate
  7. filtrationwas filtered off
  8. washwashed with a little cold THF
  9. customdried at 40° C. in vacuum

Sources & evidence

ORD record
ord-56c8eb5e913f4a4391bd94569fd25a62
Source dataset
uspto-grants-2011_07
Patent number
US07977482B2

Reaction notes

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