2,6-Dichlorobenzaldehyde → HCID 3096175, compound

HRID 1500535Notes

Reaction equation

HRID 1500535 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[S:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[S:13].C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[C:17]1[S:11][C:12](=[S:13])[NH:14][C:15]1=[O:16]

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 3096175HCID 3096175, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,6-Dichlorobenzaldehyde (77.0 g), rhodanine (58.6 g), and acetic acid (539 ml) were suspended with stirring at room temperature. Anhydrous sodium acetate (116 g) was added to the suspension, and the resulting mixture was heated under reflux for 3 hours. The reaction mixture was cooled to 45° C., and ice water (700 ml) was added. After the mixture was stirred for 0.2 hours, the precipitated crystals were collected by filtration, washed with water, and then dried to obtain 2,6-dichlorobenzylidenerhodanine. Even in non-dried form, this product could be subjected to the subsequent step.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe reaction mixture was cooled to 45° C.
  4. stirringAfter the mixture was stirred for 0.2 hours
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-66c1042d23de4925b6f63f08198741b1
Source dataset
uspto-grants-2015_12
Patent number
US09206169B2

Reaction notes

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