Pentafluorobenzaldehyde → 2,3,4,5,6-Pentafluorobenzylidene rhodanine

HRID 359550

Reaction equation

HRID 359550 reaction equation
S(C1C(F)=C(F)C(F)=C(F)C=1C(O)=O)(O)(=O)=O.FS(C1C(F)=C(F)C(F)=C(F)C=1C(F)=O)(=O)=O.[S:35]1[CH2:41][C:39](=[O:40])[NH:38][C:36]1=[S:37].[F:42][C:43]1[C:48]([CH:49]=O)=[C:47]([F:51])[C:46]([F:52])=[C:45]([F:53])[C:44]=1[F:54]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[F:42][C:43]1[C:44]([F:54])=[C:45]([F:53])[C:46]([F:52])=[C:47]([F:51])[C:48]=1[CH:49]=[C:41]1[S:35][C:36](=[S:37])[NH:38][C:39]1=[O:40]

Participants

7

Reactant 4

HCID 69558PentafluorobenzaldehydeHCID 1201546RhodanineHCID 198076532-Sulpho tetrafluorobenzoic acidHCID 198076562-Fluorosulphonyl tetrafluorobenzoyl fluoride

Product 1

HCID 49072912,3,4,5,6-Pentafluorobenzylidene rhodanineYield 73.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Production of 2-sulpho tetrafluorobenzoic acid ##STR61## and 2-fluorosulphonyl tetrafluorobenzoyl fluoride ##STR62## 38 g of triethylamine were added dropwise to a well stirred suspension of 50 g of rhodanine and 70 g of pentafluorobenzaldehyde in 100 ml of chloroform, the temperature being held below 40° C. by external cooling. After one hour, the solution was washed with dilute HCl, then water. The solvent was removed and the resultant yellow residue recrystallised from IMS/water to give 82 g of 2,3,4,5,6-pentafluorobenzylidene rhodanine having a melting point of 132-135° C.

Workup

  1. custombeing held below 40° C. by external cooling
  2. washthe solution was washed with dilute HCl
  3. customThe solvent was removed
  4. customthe resultant yellow residue recrystallised from IMS/water

Sources & evidence

ORD record
ord-0ec4dc541aa24db4ac752d485e614555
Source dataset
uspto-grants-1991_03
Patent number
US05001163

Linked notes

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