Ammonia → HCID 59420846, compound

HRID 499068Notes

Reaction equation

HRID 499068 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl.[CH:18](=O)/[CH:19]=[CH:20]/[CH3:21].N>>[CH3:18][C:19]1[CH:20]=[CH:21][C:14]2[C:13](=[CH:12][CH:11]=[C:10]([S:9][S:8][C:5]3[CH:4]=[C:3]4[C:2](=[CH:7][CH:6]=3)[N:1]=[C:3]([CH3:4])[CH:2]=[CH:7]4)[CH:15]=2)[N:16]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 128754,4'-DiaminodiphenyldisulfideHCID 447466Crotonaldehyde

Product 1

HCID 59420846HCID 59420846, compound

Procedure

To a stirred slurry of 4-aminophenyl disulfide (5.0 g, 0.02 mol) in refluxing 6M HCl (65 ml) was added crotonaldehyde (4.2 g, 0.06 mol) dropwise over 90 minutes. The resulting mixture was refluxed for an additional 2 hours, then cooled to ambient. Conc aqueous ammonia was added to adjust the pH to neutral and the mixture extracted with ethyl acetate. The combined extracts were washed with water, then saturated aqueous brine, dried (MgSO4), filtered and concentrated. The crude was purified on silica gel, eluting with 50 to 100% ethyl acetate/petrol. The product was an oil (2.57 g, 37%); MS ES+ 349.17.

Workup

  1. temperatureThe resulting mixture was refluxed for an additional 2 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialsaturated aqueous brine, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified on silica gel
  9. washeluting with 50 to 100% ethyl acetate/petrol

Sources & evidence

ORD record
ord-6c1f2bd761194c2781110c658d5e80dc
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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