3-(4-Nitrobenzyl)-thiazolidine → 3-(4-Aminobenzyl)-thiazolidine

HRID 2373757Notes

Reaction equation

HRID 2373757 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][S:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>Cl>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][S:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 219186763-(4-Nitrobenzyl)-thiazolidine

Product 1

HCID 154105273-(4-Aminobenzyl)-thiazolidineYield 63%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-(4-nitrobenzyl)-thiazolidine (1.1 g, 5 mmoles) is put into solution in 10 ml concentrated hydrochloric acid at 0° C. Dihydrated tin chloride (7.7 g, 34 mmoles) is added in portions, the mixture is heated for 2 hours under reflux and the acid is evaporated off under reduced pressure. The residue is then taken up in 20 ml of water and neutralized with a 2N soda solution (approximately 100 ml). 100 ml of dichloromethane is added to the medium and the whole is filtered on celite in order to eliminate the salts in suspension. The organic phase is extracted, washed 3 times with 50 ml of water, dried, filtered and evaporated to dryness under reduced pressure. The expected product is purified on silica gel in a dichloromethane/methanol (98/2) mixture and is obtained in the form of of a beige powder (0.6 g, 63%). Melting point: 73-74° C.

Workup

  1. temperaturethe mixture is heated for 2 hours
  2. temperatureunder reflux
  3. customthe acid is evaporated off under reduced pressure
  4. addition100 ml of dichloromethane is added to the medium
  5. filtrationthe whole is filtered on celite in order
  6. extractionThe organic phase is extracted
  7. washwashed 3 times with 50 ml of water
  8. customdried
  9. filtrationfiltered
  10. customevaporated to dryness under reduced pressure
  11. customThe expected product is purified on silica gel in a dichloromethane/methanol (98/2) mixture

Sources & evidence

ORD record
ord-9255f81437d0495aaa9c54debeafc0fe
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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