Acetic Acid → 3-Phenylmethyl-2-thiazolidinone

HRID 2108003Notes

Reaction equation

HRID 2108003 reaction equation
Br.N=[C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][S:4]1.C([O-])(=[O:17])C.[Na+].C(O)(=O)C.N([O-])=O.[Na+]>O>[C:9]1([CH2:8][N:7]2[CH2:6][CH2:5][S:4][C:3]2=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 230451002-Imino-3-phenylmethylthiazolidine hydrobromideHCID 23668193Sodium Nitrite

Product 1

HCID 109213893-Phenylmethyl-2-thiazolidinoneYield 42.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 2.73 g (0.01 mol) of 2-imino-3-phenylmethylthiazolidine hydrobromide in 10 ml of water 1.36 g of anhydrous sodium acetate and 0.62 ml of glacial acetic acid are added, then 0.75 g of sodium nitrite dissolved in 3 ml of water is dropped to the above mixture at 5° C. under stirring, then the mixture is stirred at 5° C. for additional 3 hours. After standing in a refrigerator overnight, the solution is stirred at room temperature for 3 hours. After rubbing, a precipitate appears which is filtered off, washed with water, dried and then refluxed with five volumes of n-butanol for 2 hours. After evaporating the solvent, the residue is thoroughly rubbed with diisopropyl ether and the product is filtered off. Thus, 0,81 g (42.3%) of the title product is obtained, m.p.: 49°-50° C.

Workup

  1. additionis dropped to the above mixture at 5° C.
  2. stirringthe mixture is stirred at 5° C. for additional 3 hours
  3. customAfter standing in a refrigerator overnight
  4. stirringthe solution is stirred at room temperature for 3 hours
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried
  8. temperaturerefluxed with five volumes of n-butanol for 2 hours
  9. customAfter evaporating the solvent
  10. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-f980a061cec643779b9e33f8bd6ecc4e
Source dataset
uspto-grants-1990_06
Patent number
US04937252

Reaction notes

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