1,1'-Thiocarbonyldiimidazole → 1,4-Dihydro-2,6-dimethyl-4-(3-isothiocyanatophenyl)-3,5-pyrazinedicarboxylic acid, dimethyl ester

HRID 566903Notes

Reaction equation

HRID 566903 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]2[C:20]([O:22][CH3:23])=[O:21])[CH:5]=[CH:6][CH:7]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[S:25]>CN(C=O)C>[CH3:19][C:10]1[NH:11][C:12]([CH3:18])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([N:1]=[C:24]=[S:25])[CH:3]=2)[C:9]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 155242374-(3-Aminophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyrazinedicarboxylic acid, dimethyl ester

Product 1

HCID 155242381,4-Dihydro-2,6-dimethyl-4-(3-isothiocyanatophenyl)-3,5-pyrazinedicarboxylic acid, dimethyl esterYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-(3-Aminophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyrazinedicarboxylic acid, dimethyl ester (3.8 mmol) in 16 mL of DMF was slowly added into a DMF solution (20 mL) of 1,1′-thiocarbonyldiimidazole (5.2 mmol) and the reaction went to completion in 0.5 hours. After DMF was removed in vacuo, the residue was purified by chromatography on silica gel eluted with 50% (v/v) ethyl acetate in hexanes to give the title compound as a yellow powder (1.19 g, 87%); 1H-NMR (CDCl3) δ 7.09 (t, 1H, J=8.1 Hz), 6.73 (dd, 1H, J=7.8, 1.9 Hz), 6.59 (dd, 1H, J=8.3, 2.4 Hz), 6.47 (t, 1H, J=2.1 Hz), 6.06 (s, 1H), 3.79 (s, 6H), and 2.43 (s, 6H); 13C-NMR (CDCl3) δ 166.0, 151.7, 149.1, 131.3, 129.6, 117.7, 112.6, 110.3, 108.9, 52.0, and 18.1.

Workup

  1. customAfter DMF was removed in vacuo
  2. customthe residue was purified by chromatography on silica gel
  3. washeluted with 50% (v/v) ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b9897b9df4f64abd9c5e80e9040c38a0
Source dataset
uspto-grants-2001_01
Patent number
US06177429B1

Reaction notes

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