Ammonia → HCID 10360971, compound

HRID 2396054Notes

Reaction equation

HRID 2396054 reaction equation
C[O:2][C:3](=O)[C:4]1[C:5](=[CH:10][C:11]([N:22]([CH3:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:12]([N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH:13]=1)[C:6]([O:8]C)=O.[NH3:31]>C(O)CO>[CH3:15][N:14]([C:12]1[CH:13]=[C:4]2[C:3](=[O:2])[NH:31][C:6](=[O:8])[C:5]2=[CH:10][C:11]=1[N:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:29])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10431330HCID 10431330, compound

Product 1

HCID 10360971HCID 10360971, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Analogously to Example 1, 66 mg (0.16 mmol) of 4,5-bis(N-methyl-N-phenylamino)phthalic acid dimethyl ester (Example 14 A)in 5 ml of ethylene glycol are heated at 120° and, with stirring, ammonia gas is passed through the mixture for 18 hours. The reaction mixture is cooled, and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 1:1 and the product fractions are combined and concentrated by evaporation, yielding the rifle compound in the form of slightly yellow crystals, FAB-MS: 358 [M+ +H], 1H-NMR (CDCl3): 3.05 (s, 6H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 1:1
  7. concentrationconcentrated by evaporation
  8. customyielding the rifle compound in the form of slightly yellow crystals, FAB-MS

Sources & evidence

ORD record
ord-9dc80881652f402aa4c2770a27b4dd7b
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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