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

HRID 224572Notes

Reaction equation

HRID 224572 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 (2.69 g., 0.01 mole) in 75 ml. of methyl cellosolve and adding to this stirred solution, a solution of oxalic acid dihydrate (1.26 g., 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 2.75 g. 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 2.75 g

Sources & evidence

ORD record
ord-178ee513804c4030a304b762a9e4eb4d
Source dataset
uspto-grants-1980_11
Patent number
US04233289

Reaction notes

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