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

HRID 987039Notes

Reaction equation

HRID 987039 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-91d7f1ebfb3047068a14e9a448d9c98a
Source dataset
uspto-grants-2003_10
Patent number
US06630461B2

Reaction notes

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