Chlorosulfonic acid → HCID 178464496, compound

HRID 1689563Notes

Reaction equation

HRID 1689563 reaction equation
[CH2:1]([N:3]([CH2:35][CH2:36][OH:37])[C:4]1[CH:9]=[CH:8][C:7](/[N:10]=[N:11]/[C:12]2[S:13][C:14]([CH:23]=[C:24]3[C:32](=[O:33])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]3=[O:34])=[C:15]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:16]=2)=[CH:6][CH:5]=1)[CH3:2].Cl[S:39]([OH:42])(=[O:41])=[O:40]>C1COCC1>[S:39]([OH:42])([O:37][CH2:36][CH2:35][N:3]([C:4]1[CH:5]=[CH:6][C:7](/[N:10]=[N:11]/[C:12]2[S:13][C:14]([CH:23]=[C:24]3[C:25](=[O:34])[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:32]3=[O:33])=[C:15]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:16]=2)=[CH:8][CH:9]=1)[CH2:1][CH3:2])(=[O:41])=[O:40]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 178464436HCID 178464436, compound

Product 1

HCID 178464496HCID 178464496, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.32 g (0.62 mmol) 2-{[2-((E)-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-diazenyl)-4-(1-piperidinyl)-1,3-thiazol-5-yl]methylene}-1H-indene-1,3(2H)-dione were dissolved in 33 ml THF and cooled to 0° C. Then 0.11 g (0.93 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-edbdb25a99a947f0a69e4540c94164ad
Source dataset
uspto-grants-2012_04
Patent number
US08152861B2

Reaction notes

Loading…