Dichloromethane → HCID 23335400, compound

HRID 903880Notes

Reaction equation

HRID 903880 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH3:16])[CH:11]=[C:12]([CH3:15])[N:13]=2)[CH:8]=[CH:7][C:6]1=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].C(Cl)[Cl:34].C(=O)([O-])[O-].[K+].[K+]>O>[ClH:34].[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH3:16])[CH:11]=[C:12]([CH3:15])[N:13]=2)[CH:8]=[CH:7][C:6]1=[S:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 14817Phosphorus sulfide (P2S5)HCID 23335388HCID 23335388, compound

Product 1

HCID 23335400HCID 23335400, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-dimethylaminoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one (2.5 g., 0.01 mole) and phosphorus pentasulfide (2.0 g., 0.009 mole) in 60 ml. of methylene chloride is heated at reflux for 4 hours. The reaction is cooled, water and solid potassium carbonate added, and the organic layer is separated, dried, filtered through charcoal and evaporated to dryness. The residue is dissolved in ether, hydrogen chloride is added and the salt is recrystallized from isopropanol to yield 1-(2-dimethylaminoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-thione hydrochloride m.p. 209°-211° C.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction is cooled
  3. customthe organic layer is separated
  4. customdried
  5. filtrationfiltered through charcoal
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved in ether
  8. additionhydrogen chloride is added
  9. customthe salt is recrystallized from isopropanol

Sources & evidence

ORD record
ord-959fff32704646879b42b6d9cdff2fa1
Source dataset
uspto-grants-1980_10
Patent number
US04229456

Reaction notes

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