Diisopropylcarbodiimide → ethyl (2-o-tolylamino-3H-benzimidazol-5-yl)acetate

HRID 49705Notes

Reaction equation

HRID 49705 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].[C:15]1([CH3:24])[C:16]([N:21]=[C:22]=S)=[CH:17][CH:18]=[CH:19][CH:20]=1.C(N=C=NC(C)C)(C)C>C(O)C>[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]1[NH:1][C:2]2[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 691952-Methylphenyl isothiocyanateHCID 12986345Ethyl 2-(3,4-diaminophenyl)acetate

Product 1

HCID 86586441ethyl (2-o-tolylamino-3H-benzimidazol-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3,4-diaminophenylacetate (5.8 g, prepared according to the procedure of Mederski et al, Bioorg Med Chem Left, 1998, 8, pages 17-22) and o-tolylisothiocyanate (4.9 g) in ethanol (100 mL) was kept at room temperature overnight then treated with diisopropylcarbodiimide (7.6 g). The mixture was stirred at reflux for 5 hours then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of 10% methanol and ether (1:9, v/v) to give the title compound (5.2 g) as a yellow gum.

Workup

  1. customprepared
  2. waitLeft
  3. temperatureat reflux for 5 hours
  4. customthen evaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of 10% methanol and ether (1:9, v/v)

Sources & evidence

ORD record
ord-a12a5571ce9d49c5b8ecb34baae7feb4
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

Loading…