Ammonia → HCID 178454931, compound

HRID 375053Notes

Reaction equation

HRID 375053 reaction equation
[CH2:1]([S:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]#[N:17])[C:10]([C:18]#[N:19])=[CH:9]2)[CH2:2][CH2:3][CH3:4].C[O-].[Na+].[Na].[NH3:24]>CO>[CH2:1]([S:5][C:6]1[CH:15]=[CH:14][C:13]2=[CH:12][C:11]3[C:16](=[NH:24])[NH:17][C:18](=[NH:19])[C:10]=3[CH:9]=[C:8]2[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 15014883HCID 15014883, compound

Product 1

HCID 178454931HCID 178454931, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In an atmosphere of nitrogen, 30.0 g (0.11 mole) of 6-n-butylthio-2,3-dicyanonaphthalene was added to a solution of sodium methoxide in methanol prepared by adding 1.46 g (64 mmoles) of metallic sodium in 5 portions to 350 ml of anhydrous methanol. While thoroughly stirring the mixture, anhydrous ammonia gas was slowly bubbled at room temperature over a period of about one hour. Then, the mixture was refluxed for about 3 hours, while bubbling anhydrous ammonia gas. After cooling, the yellow solid precipitated was filtered and the residue was thoroughly washed with methanol and dried under reduced pressure to obtain 30 g of 6-n-butylthio-1,3-diiminobenz[f]isoindoline as a yellow solid. FIG. 6 illustrates its IR spectrum. Without further purification, it was used in the subsequent reaction.

Workup

  1. customprepared
  2. customwas slowly bubbled at room temperature over a period of about one hour
  3. temperatureThen, the mixture was refluxed for about 3 hours
  4. customwhile bubbling anhydrous ammonia gas
  5. temperatureAfter cooling
  6. customthe yellow solid precipitated
  7. filtrationwas filtered
  8. washthe residue was thoroughly washed with methanol
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-1d6b1a00dcd54a908f6b78ca9c8eb8d9
Source dataset
uspto-grants-1996_01
Patent number
US05484685

Reaction notes

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