Dichloromethane → HCID 54067930, compound

HRID 1419878Notes

Reaction equation

HRID 1419878 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:24]=1[NH2:25].C(Cl)Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:25][C:24]1[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:23]=1[CH3:22])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 68962,6-DimethylanilineHCID 516892Sodium BicarbonateHCID 545624293-Butyryl-4-chloro-8-(2-methylthioethoxy)quinoline

Product 1

HCID 54067930HCID 54067930, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-butyryl-4-chloro-8-(2-methylthioethoxy)quinoline (0.8 g, 2.5 mmol) and 2,6-dimethylaniline (0.45 g, 3.7 mmol) in toluene (12 ml) was heated to 90° C. and stirred 3.0 h. After cooling to room temperature, methylene chloride and water were added. The mixture was neutralized with a saturated solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated. Chromatography (SiO2 ; EtOAc) gave 0.7 g (68%) of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-7e7c9eca44ea44bba0121beeee4a9bd1
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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