Thiazolidine → HCID 927517, compound

HRID 1095538Notes

Reaction equation

HRID 1095538 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[S:13]1[CH2:17][CH2:16][NH:15][CH2:14]1>C(Cl)(Cl)Cl>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:15]2[CH2:16][CH2:17][S:13][CH2:14]2)=[CH:5]1

Participants

4

Reactant 2

HCID 10444ThiazolidineHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 927517HCID 927517, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(2-Bromo-ethyl)-indole (3.00 g, 13.4 mmol) and thiazolidine (2.38 g, 26.8 mmol) were stirred in abs. CHCl3 (25 ml) at a bath temperature of 75° C. for 5 h. The mixture was cooled to RT and extracted with dilute sulfuric acid (2×30 ml). The acidic aqueous phase was rendered alkaline with 5N NaOH, while cooling with ice, and extracted with ether (3×30 ml). The organic phase was dried over Na2SO4 and concentrated i. vac. and the residue was purified by flash chromatography with CHCl3/MeOH (20:1→4:1→MeOH).

Workup

  1. extractionextracted with dilute sulfuric acid (2×30 ml)
  2. temperaturewhile cooling with ice
  3. extractionextracted with ether (3×30 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated i
  6. customand the residue was purified by flash chromatography with CHCl3/MeOH (20:1→4:1→MeOH)

Sources & evidence

ORD record
ord-5a5f34f358494d0a8b52adbe72d0a080
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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