Dimethylformamide → HCID 20144443, compound

HRID 649022Notes

Reaction equation

HRID 649022 reaction equation
[F:1][C:2]1[CH:15]=[C:14]2[C:5]([S:6](=[O:21])(=[O:20])[C:7]3[CH:8]=[C:9]([C:17](O)=[O:18])[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C[N:27](C)C=O>>[F:1][C:2]1[CH:15]=[C:14]2[C:5]([S:6](=[O:21])(=[O:20])[C:7]3[CH:8]=[C:9]([C:17]([NH2:27])=[O:18])[CH:10]=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 20144445HCID 20144445, compound

Product 1

HCID 20144443HCID 20144443, compound

Procedure

A mixture of 7-fluoro-9-oxo-3-thioxanthene carboxylic acid 10,10-dioxide (see example 6), 34.0 g (0.11 mol), and thionyl chloride, 130.9 g (1.10 mol), was heated at reflux for 2.0 hr. Dimethyl formamide, 1 ml, was added to the mixture, giving a solution which was heated at reflux overnight. The reaction was cooled, and a yellow crystalline solid, 27.85 g, was collected and washed with ether. A portion of the acid chloride, 5.0 g, was placed in concentrated NH4OH, 50 mL, and heated on a steam bath for 0.5 hr. The solid was filtered and washed with H2O and acetone to give 3.82 g of the amide. A small amount of the amide was recrystallized from DMF:MeOH/75:25 to provide 0.3 g of a light yellow crystalline 7-fluoro-9-oxothioxanthene-3-carboxamide 10,10-dioxide, m.p. 307°-310° C. TLC (CHCl3 /MeOH/9/1) Rf =0.45.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.0 hr
  3. customgiving a solution which
  4. temperaturewas heated
  5. temperatureat reflux overnight
  6. temperatureThe reaction was cooled
  7. customa yellow crystalline solid, 27.85 g, was collected
  8. washwashed with ether
  9. temperature50 mL, and heated on a steam bath for 0.5 hr
  10. filtrationThe solid was filtered
  11. washwashed with H2O and acetone

Sources & evidence

ORD record
ord-95697b21c0ef448fa81e2faf3766aaac
Source dataset
uspto-grants-1988_04
Patent number
US04737514

Reaction notes

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