Oxalic acid dihydrate → 3-pyridylmethyl N-(4-cyanophenyl)thiocarbamate oxalate

HRID 263305Notes

Reaction equation

HRID 263305 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9](=[S:19])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:2]=1.O.O.[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24]>COCCO>[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24].[C:17]([C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:9](=[S:19])[O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:12][CH:13]=1)#[N:18]

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 12790266O-[(Pyridin-3-yl)methyl] (4-cyanophenyl)carbamothioate

Product 1

HCID 205640723-pyridylmethyl N-(4-cyanophenyl)thiocarbamate oxalate

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent2×

Procedure

The oxalate salt of Example I is made by dissolving 3-pyridylmethyl-N-(4-cyanophenyl)thiocarbamate (2.69g., 0.01 mole) in 75 ml. of methyl cellosolve and adding to this stirred solution, a solution of oxalic acid dihydrate (1.26g., 0.01 mole) in 10 ml. of methyl cellosolve. The resulting thick suspension is allowed to stand at room temperature for 18 hours. The mixture is filtered and dried in vacuo to give 2.75g. melting at 189° C. with decomposition. The product structure is confirmed by infra-red spectroscopy.

Workup

  1. filtrationThe mixture is filtered
  2. customdried in vacuo
  3. customto give 2.75g

Sources & evidence

ORD record
ord-a874121e61e14a3d8359a9495aeb035d
Source dataset
uspto-grants-1979_05
Patent number
US04156780

Reaction notes

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