Acetone → HCID 19737568, compound

HRID 1110453Notes

Reaction equation

HRID 1110453 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)[CH:7]=1.[C:23]1(=[O:29])O[C:26](=[O:27])[CH:25]=[CH:24]1.C(O[C:34](=[O:36])[CH3:35])(=O)C.C(N(CC)CC)C.[CH3:44][C:45](C)=[O:46]>O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C.O>[C:45]1(=[O:46])[N:19]([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[O:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][C:4]3[CH:20]=[CH:21][CH:22]=[C:2]([N:1]4[C:23](=[O:29])[CH:24]=[CH:25][C:26]4=[O:27])[CH:3]=3)[CH:7]=2)[C:34](=[O:36])[CH:35]=[CH:44]1

Participants

8

Reactant 5

HCID 180Acetone2×HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 66342Benzenamine, 3,3'-(1,3-phenylenebis(oxy))bis-

Product 1

HCID 19737568HCID 19737568, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 62601Nickel acetate tetrahydrateCatalystHCID 962WaterSolvent

Procedure

A solution of 584 g of 1,3-bis-(3-aminophenoxy)benzene in 1,000 ml of acetone is added dropwise to a solution of 392 g of maleic anhydride and 11 g of nickel(II) acetate tetrahydrate in 1,000 ml of acetone at 10°-20° C. in the course of 1 hour. Stirring is continued for 2 hours, after which 612.6 g of acetic anhydride and 121.5 g of triethylamine are added. After heating has been carried out for 3 hours at 50° C., the mixture is cooled and 5,000 1 of water are added dropwise. The precipitated product is filtered off, washed, and dried at 70° C. under reduced pressure. 747 g (82%) of 1,3-bis-(3-maleimidophenoxy)-benzene are obtained as pale yellow crystals of melting point 138°-140° C.

Workup

  1. temperatureAfter heating
  2. waithas been carried out for 3 hours at 50° C.
  3. temperaturethe mixture is cooled
  4. filtrationThe precipitated product is filtered off
  5. washwashed
  6. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-72c0ed7707c24fe98a5da91e8925eb3b
Source dataset
uspto-grants-1990_12
Patent number
US04975506

Reaction notes

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