Diethyl squarate → HCID 89526128, compound

HRID 1528200Notes

Reaction equation

HRID 1528200 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[NH2:13][C:14]1[C:22]2[NH:21][C:20](=[O:23])[NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:9]([O:8][C:7]1[C:6](=[O:11])[C:5](=[O:12])[C:4]=1[NH:13][C:14]1[C:22]2[NH:21][C:20](=[O:23])[NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)[CH3:10]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 150200594-Amino-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 89526128HCID 89526128, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.86 ml of 3,4-diethoxycyclobut-3-ene-1,2-dione (5.9 mmol, 1.5 eq) was added to a solution of 0.59 g of 4-amino-1,3-dihydrobenzoimidazol-2-one (4.0 mmol, 1 eq) in 21 ml of ethanol. The reaction medium was stirred at ambient temperature for 2 days (formation of a precipitate). Ethanol was added in order to promote the fall of the precipitate, which was filtered off, washed with diethyl ether and dried under vacuum at 45° C. The residue was chromatographed on silica gel, eluted with 90/10 dichloromethane/methanol. 0.42 g of product was obtained in the form of a white solid. Yield=38.6%.

Workup

  1. filtrationwas filtered off
  2. washwashed with diethyl ether
  3. customdried under vacuum at 45° C
  4. customThe residue was chromatographed on silica gel
  5. washeluted with 90/10 dichloromethane/methanol

Sources & evidence

ORD record
ord-9982981d992f48b9bd58f9657e02f83c
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

Loading…