1,1-Diethoxy-2-isothiocyanatoethane → N-(2,2-diethoxyethyl)-N'-(6-fluoro-2-methylquinolin-5-yl)thiourea

HRID 1285494Notes

Reaction equation

HRID 1285494 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2.[CH2:14]([O:16][CH:17]([O:22][CH2:23][CH3:24])[CH2:18][N:19]=[C:20]=[S:21])[CH3:15]>C(O)C>[CH2:23]([O:22][CH:17]([O:16][CH2:14][CH3:15])[CH2:18][NH:19][C:20]([NH:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:13])=[N:7]2)=[S:21])[CH3:24]

Participants

4

Reactant 2

HCID 3776081,1-Diethoxy-2-isothiocyanatoethaneHCID 128968136-Fluoro-2-methylquinolin-5-amine

Product 1

HCID 13338833N-(2,2-diethoxyethyl)-N'-(6-fluoro-2-methylquinolin-5-yl)thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 17.85 g (0.1013 mole) of 5-amino-6-fluoro-2-methylquinoline was added 19.5 g (0.1114 mole) of 2,2-diethoxyethylisothiocyanate and the mixture was heated at 80°-90° C. for 1.5 hours. The residue was slurried in ethanol, separated by filtration, washed with ethanol and then recrystallized from ethanol to provide N-(2,2-diethoxyethyl)-N'-(6-fluoro-2-methylquinolin-5-yl)thiourea, m.p. 189°-191° C. Analysis: Calculated for C17H22FN3O2S: %C, 58.1; %H, 6.3; %N, 12.1; Found: %C, 58.3; %H, 6.5; %N, 11.9.

Workup

  1. temperaturethe mixture was heated at 80°-90° C. for 1.5 hours
  2. customseparated by filtration
  3. washwashed with ethanol
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-616f418eb410436ab51c098ca59929fd
Source dataset
uspto-grants-1986_01
Patent number
US04567269

Reaction notes

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