Dimethyl Sulfoxide → HCID 13983452, compound

HRID 580456Notes

Reaction equation

HRID 580456 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6](Cl)=[CH:7][CH:8]=2)[N:3]=1.Cl.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][SH:18].[OH-].[K+].CS(C)=O>C(O)C>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([S:18][CH2:17][CH2:16][N:15]([CH3:19])[CH3:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 25798Captamine HydrochlorideHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983452HCID 13983452, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture composed of 2-amino-7-chloro-1,8-naphthyridine (29.6 g), 2-dimethylaminoethanethiol hydrochloride (48 g), potassium hydroxide pellets (85% pure; 43.5 g) and dimethyl sulphoxide (300 cc) is heated for 2 hours at 90° C. The reaction mixture is then poured into distilled water (400 cc) and extracted with methylene chloride (6×250 cc). The extracts are washed with distilled water (300 cc), dried over magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure. The residue obtained is taken up with ethanol (100 cc) and the insoluble product is separated by filtration, washed with ethanol (2×30 cc) and dried at 40° C. under reduced pressure (0.07 kPa). 2-Amino-7-(2-dimethylaminoethylthio)-1,8-naphthyridine (22 g), m.p. 174° C., is obtained.

Workup

  1. additionThe reaction mixture is then poured
  2. distillationinto distilled water (400 cc)
  3. extractionextracted with methylene chloride (6×250 cc)
  4. washThe extracts are washed with distilled water (300 cc)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness at 40° C. under reduced pressure
  7. customThe residue obtained
  8. customthe insoluble product is separated by filtration
  9. washwashed with ethanol (2×30 cc)
  10. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-81d1b0a9cfc640feb81cbdbe2d12213f
Source dataset
uspto-grants-1988_06
Patent number
US04753933

Reaction notes

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