2-(2,4-Dichlorobenzylidene)-3-oxobutanamide → HCID 136393283, compound

HRID 1868479Notes

Reaction equation

HRID 1868479 reaction equation
[NH2:1][C:2]1[NH:3][CH:4]=[C:5]([S:7]([OH:10])(=[O:9])=[O:8])[N:6]=1.[Cl:11][C:12]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:13]=1[CH:14]=[C:15]([C:19](=O)[CH3:20])[C:16]([NH2:18])=[O:17]>CCO.O>[C:16]([C:15]1[CH:14]([C:13]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:12]=2[Cl:11])[N:3]2[CH:4]=[C:5]([S:7]([OH:10])(=[O:9])=[O:8])[N:6]=[C:2]2[NH:1][C:19]=1[CH3:20])(=[O:17])[NH2:18]

Participants

4

Reactant 2

HCID 34229192-(2,4-Dichlorobenzylidene)-3-oxobutanamideHCID 178509073HCID 178509073, compound

Product 1

HCID 136393283HCID 136393283, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-amino-1H-imidazole-4-sulfonic acid (82 mg, 0.5 mmol) and 2-(2,4-dichlorobenzylidene)-3-oxobutanamide (125 mg, 0.5 mmol) in 3:1 EtOH/H2O (2 mL) was heated to 80° C. for 14 h. After removal of solvent, the residue was dissolved in 1N NaOH and extracted with EtOAc (5 mL×2). The aqueous solution was then acidified with conc. HCl to pH=1. The precipitation which had formed was collected and further washed with H2O. After drying in vacuo, 6-carbamoyl-5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2-sulfonic acid was obtained a yellow solid (97 mg, 48%).

Workup

  1. customAfter removal of solvent
  2. dissolutionthe residue was dissolved in 1N NaOH
  3. extractionextracted with EtOAc (5 mL×2)
  4. customThe precipitation which
  5. customhad formed
  6. customwas collected
  7. washfurther washed with H2O
  8. customAfter drying in vacuo

Sources & evidence

ORD record
ord-a6a88416c0e14acdb7cdddbb80f4724d
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

Loading…