Ammonia → HCID 58832864, compound

HRID 902096Notes

Reaction equation

HRID 902096 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.Cl.[Br:14][C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([C:22]2[CH:23]=[C:24]3[N:32]4[C:27](=[CH:28][C:29]([CH3:33])=[N:30][C:31]=24)[N:26]([CH:34]([CH2:38][CH2:39][CH3:40])[CH2:35][CH2:36][CH3:37])[C:25]3=[NH:41])=[C:17]([CH3:42])[CH:16]=1.C([N:46](CC)C(C)C)(C)C.N>C(Cl)(Cl)Cl.O>[Br:14][C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([C:22]2[CH:23]=[C:24]3[N:32]4[C:27](=[CH:28][C:29]([CH3:33])=[N:30][C:31]=24)[N:26]([CH:34]([CH2:38][CH2:39][CH3:40])[CH2:35][CH2:36][CH3:37])[C:25]3=[N:41][C:5]([NH2:46])=[O:11])=[C:17]([CH3:42])[CH:16]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 69312803HCID 69312803, compound

Product 1

HCID 58832864HCID 58832864, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of triphosgene (1.82 g) in chloroform (9 mL) was added dropwise a solution of 4-(4-bromo-2,6-dimethyl-phenyl)-6-methyl-1-(1-propyl-butyl)-1H-1,5,7b-triaza-cyclopenta[cd]inden-2-ylideneamine hydrochloride (300 mg) synthesized by the same procedure as in example 1 and N,N-diisopropylethylamine (174 mg) in chloroform (3 mL) in an ice-cooling bath and stirred at room temperature for 1 hour. The reaction mixture was added dropwise into 25% an aqueous NH3 solution (10 mL) in an ice-cooling bath and stirred at room temperature for 2 hours. The reaction mixture was poured into H2O and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1) to give a solid. The solid was washed with diisopropylether and the title compound (42 mg) was obtained.

Workup

  1. temperaturecooling bath
  2. temperaturecooling bath
  3. stirringstirred at room temperature for 2 hours
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1)
  10. customto give a solid
  11. washThe solid was washed with diisopropylether

Sources & evidence

ORD record
ord-ab29907d85264f17a928220ea67d841a
Source dataset
uspto-grants-2008_04
Patent number
US07365078B2

Reaction notes

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