3-Hydroxy-2-naphthoic acid → HCID 20495683, compound

HRID 1292496Notes

Reaction equation

HRID 1292496 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1.C([O-])(=O)C.[Na+].[OH:17][C:18]1[C:19]([C:28](Cl)=[O:29])=[CH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2.OC1C(C(O)=O)=CC2C(C=1)=CC=CC=2>ClC1C=CC=CC=1.CN(C=O)C>[OH:17][C:18]1[C:19]([C:28]([NH:1][C:2]2[CH:11]=[CH:10][C:5]3=[N:6][C:7](=[O:9])[N:8]=[C:4]3[CH:3]=2)=[O:29])=[CH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2

Participants

7

Reactant 4

HCID 71043-Hydroxy-2-naphthoic acidHCID 517045Sodium AcetateHCID 128963863-Hydroxynaphthalene-2-carbonyl chlorideHCID 152505475-amino-2H-1,3-benzodiazol-2-one

Product 1

HCID 20495683HCID 20495683, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
20 °C

Procedure

75.0 g (0.5 mol) of 5-aminobenzimidazolone and 41 g of anhydrous sodium acetate are initially introduced into 700 ml of N,N'-dimethylformamide and 776.8 g of 3-hydroxy-2-naphthoyl chloride (from 99.0 g (0.52 mol) of 3-hydroxy-2-naphthoic acid) in chlorobenzene are metered in at 5°-10° C. in the course of 30 min. After addition is complete, the mixture is subsequently stirred at 20° C. for 3 h, warmed to 50° C. and filtered. The filter cake does not filter off with suction very well (suction time: 14 h). For purification, the filter cake is taken up in 1 ml of methanol, the mixture is stirred and filtered off with suction, and the filter cake is washed with 250 ml of methanol and subsequently several times with a total of 1 l of boiling water. After drying, 130.3 g of 3-hydroxy-N-benzimidazolon-5-yl-2-naphthamide are obtained; this corresponds to 81.7% of theory.

Workup

  1. customare metered in at 5°-10° C. in the course of 30 min
  2. additionAfter addition
  3. temperaturewarmed to 50° C.
  4. filtrationfiltered
  5. filtrationThe filter cake does not filter off with suction very well (suction time: 14 h)
  6. customFor purification
  7. stirringthe mixture is stirred
  8. filtrationfiltered off with suction
  9. washthe filter cake is washed with 250 ml of methanol and subsequently several times with a total of 1 l of boiling water
  10. customAfter drying

Sources & evidence

ORD record
ord-31123cbae3774c559ed61a326f8fa5b2
Source dataset
uspto-grants-1998_05
Patent number
US05756757

Reaction notes

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