Methyl isothiocyanate → 1-{2-[(N-methylthiocarbamoyl)amino]ethyl}-5,7-dimethyl-1,8-naphthyridin-2(1H)-one

HRID 903878Notes

Reaction equation

HRID 903878 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[C:11]([CH3:14])[N:12]=2)[CH:7]=[CH:6][C:5]1=[O:16].[CH3:17][N:18]=[C:19]=[S:20]>O>[CH3:17][NH:18][C:19]([NH:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[C:11]([CH3:14])[N:12]=2)[CH:7]=[CH:6][C:5]1=[O:16])=[S:20]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 233353721-(2-aminoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 233353811-{2-[(N-methylthiocarbamoyl)amino]ethyl}-5,7-dimethyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the free base of 1-(2-aminoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one (700 mg., 0.0032 mole) as prepared in Example 12 and methyl isothiocyanate (180 mg., 0.004 mole) in 5 ml. of water is heated at reflux for 30 minutes. On cooling the reaction, the product is collected by filtration. After recrystallization from methanol, 1-{2-[(N-methylthiocarbamoyl)amino]ethyl}-5,7-dimethyl-1,8-naphthyridin-2(1H)-one m.p. 216.5°-218° C. is obtained.

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureOn cooling
  3. customthe reaction
  4. filtrationthe product is collected by filtration
  5. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-ff828f2ff1bf4de3a3b03b88a1ed734d
Source dataset
uspto-grants-1980_10
Patent number
US04229456

Reaction notes

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