1,1'-Thiocarbonyldiimidazole → HCID 14458975, compound

HRID 1639319Notes

Reaction equation

HRID 1639319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][NH:6][C:7]([C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[NH:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[S:8].C1N=CN([C:31](N2C=NC=C2)=[S:32])C=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[C:7](=[S:8])[C:9]2[C:10](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:31]1=[S:32]

Participants

3

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 19838809HCID 19838809, compound

Product 1

HCID 14458975HCID 14458975, compoundYield 12.7%

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-[2-{N-(3,4-dichlorobenzyl)thiocarbamoyl}anilino]acetate (4.0 g) and N,N'-thiocarbonyldiimidazole (8.97 g) was heated at 120° C. for 15 minutes, and the reaction mixture was chromatographed on silica gel (100 g) eluting with chloroform. The fractions containing the desired compound were combined and concentrated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and hexane to give ethyl 2-[3-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydro-2,4-dithioxoquinazolin-1-yl]acetate (560 mg).

Workup

  1. customthe reaction mixture was chromatographed on silica gel (100 g)
  2. washeluting with chloroform
  3. additionThe fractions containing the desired compound
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-41cbca30e938421d903429ac10fa7189
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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