Ammonia → HCID 10064134, compound

HRID 2413903Notes

Reaction equation

HRID 2413903 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([S:18][CH:19]([CH3:21])[CH3:20])[N:12]4SC(C)C)[CH:5]=[C:4]([CH3:26])[CH2:3]1.[I-].[K+].N>Cl.C(O)C.O.C(OCC)(=O)C>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[C:13]([S:18][CH:19]([CH3:20])[CH3:21])[NH:12]4)[CH:5]=[C:4]([CH3:26])[CH2:3]1

Participants

8

Reactant 3

HCID 222AmmoniaHCID 4875Potassium IodideHCID 57081205HCID 57081205, compound

Product 1

HCID 10064134HCID 10064134, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Product I (2 g) was dissolved in a solution of 5N HCl (50 ml) and ethanol (10 ml). After adding potassium iodide (1.33 g), the mixture was refluxed for one hour then diluted with water, basified with concentrated ammonia solution (specific gravity 0.88) and extracted with dichloromethane three times. The dichloromethane extracts were washed (H2O), dried (MgSO4) and evaporated to give a black oil. The oil was dissolved in ethyl acetate and chromatographed over neutral alumina (grade III) eluting with ethyl acetate to give a further sample of II as a yellow solid.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. extractionextracted with dichloromethane three times
  3. washThe dichloromethane extracts were washed (H2O)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a black oil
  7. customchromatographed over neutral alumina (grade III)
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e6480429790448b68b9391b30522b868
Source dataset
uspto-grants-1988_01
Patent number
US04720498

Reaction notes

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