Dimethyl Sulfoxide → HCID 13983453, compound

HRID 580457Notes

Reaction equation

HRID 580457 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.[CH3:13][N:14]([CH3:19])[CH2:15][CH2:16][CH2:17][SH:18].[OH-].[K+].CS(C)=O>C(OCC)C.O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([S:18][CH2:17][CH2:16][CH2:15][N:14]([CH3:19])[CH3:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 30169983-(DIMETHYLAMINO)-1-PROPANETHIOL

Product 1

HCID 13983453HCID 13983453, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

A mixture composed of 2-amino-7-chloro-1,8-naphthyridine (8 g), 3-dimethylaminopropanethiol (11.4 g), potassium hydroxide pellets (85% pure; 6.26 g) and dimethyl sulphoxide (87 cc) is heated to 90° C. for 3 hours 30 minutes. The reaction mixture is then poured into water (1500 cc) and extracted with methylene chloride (5×400 cc). The organic extracts are combined and washed with distilled water (400 cc), dried over magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure (4 kPa). The residue obtained is treated with ethyl ether (100 cc). The insoluble product is separated by filtration, washed with ethyl ether (10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). 2-Amino-7-(3-dimethylaminopropylthio)-1,8-naphthyridine (9 g), m.p. 164° C., is obtained.

Workup

  1. extractionextracted with methylene chloride (5×400 cc)
  2. washwashed with distilled water (400 cc)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness at 40° C. under reduced pressure (4 kPa)
  5. customThe residue obtained
  6. customThe insoluble product is separated by filtration
  7. washwashed with ethyl ether (10 cc)
  8. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-77a231e5c32c46cca405cb6342534dc7
Source dataset
uspto-grants-1988_06
Patent number
US04753933

Reaction notes

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