Thiophosgene → HCID 18465370, compound

HRID 1416906Notes

Reaction equation

HRID 1416906 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([F:13])[CH:3]=1.[C:14](Cl)(Cl)=[S:15].[OH-].[Na+]>O.Cl>[F:13][C:4]1[CH:3]=[C:2]([N:1]=[C:14]=[S:15])[C:11]([CH3:12])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

6

Reactant 3

HCID 10040Thiophosgene2×HCID 14798Sodium HydroxideHCID 18465378HCID 18465378, compound

Product 1

HCID 18465370HCID 18465370, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 7-amino-5-fluoro-8-methylquinoline (0.39 g) and thiophosgene (0.2 mL) in water (5 mL) and 1N hydrochloric acid (5 mL) is stirred at room temperature for 1.5 hours. An additional amount of thiophosgene (0.1 mL) is added and the mixture stirred another hour. The mixture is treated with 1N sodium hydroxide (25 mL) and extracted with methylene chloride (4×50 mL). The combined extracts are dried over sodium sulfate and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 15% ethyl acetate/hexanes, to afford 5-fluoro-7-isothiocyanato-8-methylquinoline as a tan solid.

Workup

  1. stirringthe mixture stirred another hour
  2. extractionextracted with methylene chloride (4×50 mL)
  3. dry with materialThe combined extracts are dried over sodium sulfate and rotary evaporated
  4. customThe residue is purified by flash chromatography on silica gel
  5. washeluting with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c45bcae1c3e347af95c7ed4a9582e1f0
Source dataset
uspto-grants-1999_06
Patent number
US05916900

Reaction notes

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