Tetrahydrofuran → HCID 86708816, compound

HRID 2179486Notes

Reaction equation

HRID 2179486 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.O1CCCC1>O>[OH2:13].[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]\[C:12]([OH:14])=[O:13])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 18873877(2Z)-4-[(4-Aminophenyl)amino]-4-oxo-2-butenoic acid

Product 1

HCID 86708816HCID 86708816, compoundYield 166.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, into a reaction vessel were charged 13.0 g (0.12 mol) of 1,4-phenylenediamine and 140 ml of tetrahydrofuran. A solution prepared by dissolving 11.77 g (0.12 mol) of maleic anhydride in 25 ml of tetrahydrofuran was dropped into this under cooling with ice over a period of about 1 hour, then, the mixture was stirred at room temperature overnight. After completion of the reaction, the deposited crystal was isolated by filtration, and dried to obtain 24.20 g of coarse (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid as an orange powder. To 24.2 g of coarse (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid were added 250 ml of tetrahydrofuran and 50 ml of water, and the mixture was stirred at room temperature for 2 hours, then, isolated by filtration, and the filtrated material was washed twice with 20 ml of 50% tetrahydrofuran water. The resultant crystal was dried at 40° C. for 5 hours, to obtain 21.96 g of (2Z)-4-[(4-aminophenyl)amino]-4-oxo-2-butenoic acid mono-hydrate as a yellow-orange powder. Yield: 81.5%.

Workup

  1. customisolated by filtration
  2. washthe filtrated material was washed twice with 20 ml of 50% tetrahydrofuran water
  3. customThe resultant crystal was dried at 40° C. for 5 hours

Sources & evidence

ORD record
ord-7580d453573d4327828e264856ebf85d
Source dataset
uspto-grants-2015_06
Patent number
US09068055B2

Reaction notes

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