Dimethylformamide → HCID 13474436, compound

HRID 542826Notes

Reaction equation

HRID 542826 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[NH:20]1[CH2:25]CSC[CH2:21]1.CN(C)C=O>O>[CH3:21][N:20]([CH3:25])[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:13]3[N:17]([CH3:18])[N:16]=[N:15][N:14]=3)=[CH:8][N:9]2[CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67164ThiomorpholineHCID 134744537-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone

Product 1

HCID 13474436HCID 13474436, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone (10 g), thiomorpholine (10 g) and dimethylformamide (20 ml) was heated at 100° for 22 hours and then at 140° for 5.5 hours. The mixture was cooled and poured into water (220 ml). The resulting precipitate was collected and purified by high performance liquid chromatography on silica using dichloromethane:industrial methylated spirit:isopropanol 98.25:0.5:1.25 as the eluent. This gave the novel compound 7-dimethylamino-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone, m.p. 280°-283°.

Workup

  1. temperaturewas heated at 100° for 22 hours
  2. temperatureThe mixture was cooled
  3. customThe resulting precipitate was collected
  4. custompurified by high performance liquid chromatography on silica

Sources & evidence

ORD record
ord-febe3aa6486146f6b23ac69121d21199
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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