Oxalic Acid → 18257-23-3

HRID 1665204Notes

Reaction equation

HRID 1665204 reaction equation
ClC1C=C(N2C(C)=NC(S)=N2)C=CC=1Cl.C(=O)([O-])[O-].[K+].[K+].Cl.ClCC[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>CO.O.CCOCC.CCOC(C)=O>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178433554HCID 178433554, compound

Product 1

HCID 2331578918257-23-3Yield 267.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3,4-dichlorophenyl)-5-methyl-1H-1,2,4-triazole-3-thiol (0.4 mmol) was dissolved in methanol (100 mL) at room temperature. A solution of potassium carbonate in water was added dropwise until pH 9. After 15 min. under stirring a solution of 4-(2-chloroethyl)morpholine hydrochloride (0.4 mmol) in water (20 mL) was added. The reaction was left under stirring at room temperature overnight. The methanol was evaporated and after extraction with CH2Cl2 the organic layer was dried over magnesium sulphate then evaporated and finally purified by chromatographic column to give a dark orange oil. The purified product was dissolved in ether (20 mL) and mixed with a solution of oxalic acid (0.31 mmol) in EtOAc (5 mL) to give 4-(2-(3,4-dichlorophenyl)-5-methyl-1H-1,2,4-triazole-3-ylthio)ethyl)morpholine oxalate (0.147 g, yield=84%) as a white precipitate which was filtered off and dried in vacuo. H1NMR (300 MHz, DMSO, 25° C.) δ: 7.93 (d, J=2.4 Hz, 1H); 7.82 (d, J=8.7 Hz, 1H); 7.61 (dd, J=2.4 Hz, J=8.6 Hz, 1H); 3.66 (t, J=4.6 Hz, 4H); 3.32 (t, J=6.8 Hz, 2H); 2.983 (t, J=7.0 Hz, 2H); 2.78 (brs, 4H); 2.47 (s, 3H) ppm. EM (ES+) m/z=373 (100%) [M+H]+. C17H20Cl2N4O5S (463.0) calc. C, 44.07%; H, 4.35%; N, 12.09%; S=6.92%. found C, 43.79%; H, 4.60%; N, 11.87%; S,=6.75%.

Workup

  1. additionwas added
  2. waitThe reaction was left
  3. customThe methanol was evaporated
  4. extractionafter extraction with CH2Cl2 the organic layer
  5. dry with materialwas dried over magnesium sulphate
  6. customthen evaporated
  7. customfinally purified by chromatographic column
  8. customto give a dark orange oil

Sources & evidence

ORD record
ord-98ec1b4fb8b64c419e18e10a3e18e197
Source dataset
uspto-grants-2011_10
Patent number
US08039497B2

Reaction notes

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