Diethanolamine → HCID 10490463, compound

HRID 1458717Notes

Reaction equation

HRID 1458717 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH:12]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:14][OH:15].CCCCCC.C(OCC)(=O)C>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:14][OH:15]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 21226206Ethyl acetate hexane

Product 1

HCID 10490463HCID 10490463, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

In 4 ml of DMSO, 5.0 g (31.4 mmol) of 3,4-difluoronitrobenzene and 8.3 g (78.5 mmol) of diethanolamine were dissolved, followed by stirring under heat at 140° C. for one hour. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated. To the reddish brown syrup so obtained, n-hexane/ethyl acetate was added for crystallization, whereby 6.93 g of the title compound were obtained as yellow powder (yield: 90%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. customTo the reddish brown syrup so obtained

Sources & evidence

ORD record
ord-04f1b7bfebaf473f96cdd843dfda781b
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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