Triethylamine → HCID 54117166, compound

HRID 1459672Notes

Reaction equation

HRID 1459672 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23].C(N(CC)CC)C>CN(C)C=O.CS(C)=O>[N+:19]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:22]([O-:24])=[O:23])[C:13]=1[NH:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 118141-Chloro-2,6-dinitrobenzeneHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 54117166HCID 54117166, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

3.0 g (19.3 mmol) of 2-amino-5-fluorobenzoic acid and 5.88 g (29.0 mmol) of 1-chloro-2,6-dinitrobenzene were dissolved in a mixture of 30 ml of dimethylformamide with 30 ml of dimethyl sulfoxide. After adding 6.74 ml of triethylamine, the reaction mixture was stirred in a nitrogen atmosphere at room temperature for 14 days and concentrated followed by the addition of 1N hydrochloric acid thereto. Then it was extracted with ethyl acetate, washed with 1N hydrochloric acid and dried over magnesium sulfate. After concentrating, chloroform was added thereto. The crystals thus precipitated were collected. Thus 2.65 g of the title compound was obtained.

Workup

  1. concentrationconcentrated
  2. additionfollowed by the addition of 1N hydrochloric acid
  3. extractionThen it was extracted with ethyl acetate
  4. washwashed with 1N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentrating
  7. additionchloroform was added
  8. customThe crystals thus precipitated
  9. customwere collected

Sources & evidence

ORD record
ord-996bc2c7a1644464af77cb241cd483b3
Source dataset
uspto-grants-1998_12
Patent number
US05854274

Reaction notes

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