Furfurylamine → HCID 21393685, compound

HRID 461440Notes

Reaction equation

HRID 461440 reaction equation
FC1C=C(C2C=CC=CC=2)C(S(N)(=O)=O)=CC=1S(N)(=O)=O.C(N)C1OC=CC=1.C([NH:35][C:36]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:39]([S:48]([NH2:51])(=[O:50])=[O:49])=[CH:38][C:37]=1[S:52]([NH2:55])(=[O:54])=[O:53])C1OC=CC=1.FC(F)(F)C(O)=O>C(O)(=O)C>[NH2:35][C:36]1[CH:41]=[C:40]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:39]([S:48]([NH2:51])(=[O:50])=[O:49])=[CH:38][C:37]=1[S:52]([NH2:55])(=[O:54])=[O:53]

Participants

6

Reactant 4

HCID 3438FurfurylamineHCID 6422Trifluoroacetic acidHCID 21393680HCID 21393680, compoundHCID 21393687HCID 21393687, compound

Product 1

HCID 21393685HCID 21393685, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.68 G. of 4-fluoro-6-phenyl-1,3-benzenedisulfonamide and 3.1 g. of furfurylamine is heated to 95° C. for 1 1/2 hours. This mixture is cooled in ice, diluted with 30 ml. of ice water and acidified with acetic acid affording a brown precipitate of 4-furfurylamino-6-phenyl-1,3-benzenedisulfonamide which is collected by filtration and dried affording 2.14 g. of material with a m.p. of 168° to 171° C. This material is stirred with 22 ml. of trifluoroacetic acid at room temperature for 1 hour. The trifluoroacetic acid is removed in vacuo and the residue treated with 100 ml. of water and extracted with ethylacetate. The ethylacetate is dried and evaporated to dryness in vacuo affording 2.6 g. of material which is purified on a chromatography column of silica gel affording 1.6 g. of a light foam. This material is crystallized from water affording 4-amino-6-phenyl-1,3-benzenedisulfonamide with a m.p. of 197° to 198° C.

Workup

  1. temperatureThis mixture is cooled in ice
  2. additiondiluted with 30 ml
  3. filtrationis collected by filtration
  4. customdried
  5. customaffording 2.14 g
  6. customThe trifluoroacetic acid is removed in vacuo
  7. additionthe residue treated with 100 ml
  8. extractionof water and extracted with ethylacetate
  9. dry with materialThe ethylacetate is dried
  10. customevaporated to dryness in vacuo
  11. customaffording 2.6 g
  12. customof material which is purified on a chromatography column of silica gel affording 1.6 g
  13. customThis material is crystallized from water

Sources & evidence

ORD record
ord-894d9ef336854ef19902871fef23574b
Source dataset
uspto-grants-1977_12
Patent number
US04062952

Reaction notes

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