1,1'-Thiocarbonyldiimidazole → HCID 178468777, compound

HRID 1533791Notes

Reaction equation

HRID 1533791 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:13])=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].[C:14](N1C=CN=C1)(N1C=CN=C1)=[S:15]>O1CCCC1>[SH:15][C:14]1[NH:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7]=2[N:13]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 11171330Ethyl 2,3-diaminobenzoate

Product 1

HCID 178468777HCID 178468777, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethoxycarbonyl-1,2-phenylenediamine (790 mg) in tetrahydrofuran (10 ml) was added 1,1′-thiocarbonyldiimidazole (1.02 g) in ice water bath and the mixture was stirred for 20 hours at ambient temperature. The reaction solvent was concentrated in vacuo and the residue was washed with chloroform and collected by vacuum filtration to give ethyl 2-mercapto-1H-benzimidazole-4-carboxylate (665 mg).

Workup

  1. concentrationThe reaction solvent was concentrated in vacuo
  2. washthe residue was washed with chloroform
  3. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-b49681ba4cb141149e3be3df59aa54ea
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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