Dichloromethane → HCID 54270912, compound

HRID 743124Notes

Reaction equation

HRID 743124 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].[Cl:22][C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:30](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:29][C:28]1[C:23]([Cl:22])=[CH:24][CH:25]=[CH:26][C:27]=1[CH3:30])=[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 72402-ChloroanilineHCID 516892Sodium BicarbonateHCID 545624293-Butyryl-4-chloro-8-(2-methylthioethoxy)quinoline

Product 1

HCID 54270912HCID 54270912, compoundYield 72%

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-methyl, 6-chloroaniline (0.52 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 0.77 g (72%) 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-0084837c3c21459798da5d7b6a77616d
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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