1,3-Thiazolidine-2-carboxylic acid → HCID 21941438, compound

HRID 1158911Notes

Reaction equation

HRID 1158911 reaction equation
[S:1]1[CH2:5][CH2:4][NH:3][CH:2]1[C:6]([OH:8])=[O:7].[N:9]([O-])=[O:10].[Na+]>C(O)(=O)C.O>[N:9]([N:3]1[CH2:4][CH2:5][S:1][CH:2]1[C:6]([OH:8])=[O:7])=[O:10]

Participants

5

Reactant 2

HCID 424861,3-Thiazolidine-2-carboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 21941438HCID 21941438, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of thiazolidine-2-carboxylic acid (39.9 g, 0.30 mol) in 1,000 ml of acetic acid was added a solution of 31.0 g (0.45 mol) of sodium nitrite in 500 ml of water over 13 minutes at room temperature and stirred for 5 hours. The reaction solution was concentrated under reduced pressure. Acetone (500 ml) was added to the residue and the precipitate was filtered through a pad of Celite. The pad was washed with acetone (500 ml). The filtrate was concentrated under reduced pressure to dryness and crude 3-nitrosothiazolidin-2-carboxylic acid was obtained as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionAcetone (500 ml) was added to the residue
  3. filtrationthe precipitate was filtered through a pad of Celite
  4. washThe pad was washed with acetone (500 ml)
  5. concentrationThe filtrate was concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-f89682de5fba4ea2b5f05909ee126eac
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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