Trimethylamine → HCID 23368874, compound

HRID 1901961Notes

Reaction equation

HRID 1901961 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:10]=[C:11]([C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([NH2:29])[CH:20]=2)[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1.[CH3:30]N(C)C.[O-2].[Mg+2].C(O[C:40](=[O:42])[CH3:41])(=O)C.CN(C)[CH:45]=[O:46]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O>[C:45]1(=[O:46])[N:29]([C:21]2[CH:20]=[C:19]([C:11]3[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=[C:9]([N:8]4[C:1](=[O:7])[CH:2]=[CH:3][C:4]4=[O:5])[CH:10]=3)[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=2)[C:40](=[O:42])[CH:41]=[CH:30]1

Participants

9

Reactant 6

HCID 1146TrimethylamineHCID 6228Dimethylformamide3×HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 6850729Magnesium monoxideHCID 22020412HCID 22020412, compound

Product 1

HCID 23368874HCID 23368874, compound

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 962WaterSolvent2×

Procedure

10.8 g (110 mmol) of maleic anhydride was dissolved with stirring into 50 mL of N,N'-dimethylformamide in a flask. To the resulting solution was slowly dripped a solution of 16.0 g (50.0 mmol) of 3,3'-diamino-5,5'-bis(trifluoromethyl)biphenyl (6FmBPDA) in 50 mL of dimethyl formamide from a dropping funnel. After stirring the resultant solution for 3 hours, 2.4 g of trimethylamine, 100 mg of magnesium (II) oxide and 10 mg of cobalt (II) acetate tetrahydrate were added to the solution. Subsequently, 13 g of acetic anhydride was dripped at room temperature from a dropping funnel over a period of 30 minutes, and the resultant solution was stirred for three hours. To this reaction solution was added little by little one litter of water, thus precipitating crude crystals which was then taken out through filtration. The crude crystals thus obtained was dissolved into a little amount of dimethyl formamide, and the solution was poured into one litter of water thereby precipitating crystallized product. The same procedure was repeated once more thereby obtaining refined crystals which were then taken out through filtration. The refined crystals were vacuum-dried to obtain the aimed compound (6FmBPDM).

Workup

  1. customthus precipitating crude crystals which
  2. filtrationwas then taken out through filtration
  3. customThe crude crystals thus obtained
  4. customthereby precipitating
  5. customcrystallized product
  6. customThe same procedure was repeated once more thereby obtaining refined crystals which
  7. filtrationwere then taken out through filtration
  8. customThe refined crystals were vacuum-dried

Sources & evidence

ORD record
ord-3c1a17a102f24503b075bcd1beb1b3bf
Source dataset
uspto-grants-1996_11
Patent number
US05578697

Reaction notes

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