Dimethylformamide → HCID 69900232, compound

HRID 1884227Notes

Reaction equation

HRID 1884227 reaction equation
[F:1][CH:2]([F:31])[O:3][CH:4]=[C:5]([C:21]1[CH:30]=[CH:29][C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[CH:22]=1)[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:7].[CH3:32]N(C)C=O.[H-].[Na+].CI>O>[F:1][CH:2]([F:31])[O:3][CH:4]=[C:5]([C:21]1[CH:30]=[CH:29][C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[CH:22]=1)[C:6]([N:8]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH3:32])=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69898734HCID 69898734, compound

Product 1

HCID 69900232HCID 69900232, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Five hundred milligrams (500 mg) of 3-difluoromethoxy-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide (1.16 mmol) and 5 ml of anhydrous N,N-dimethylformamide were mixed and cooled, and then 49 mg (1.22 mmol) of 60% sodium hydride was added thereto and stirred at 0° C. for 30 minutes. To the mixture, 164 mg (1.16 mmol) of methyl iodide was added and stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. Water was added to the reaction mixture, which which was followed by extracted with ethyl acetate, washed with 5% hydrochrolic acid and saturated brine subsequently, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel preparative thin layer chromatography (eluent, hexane:ethyl acetate=3:1) to give 460 mg of 3-difluoromethoxy-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide (the present compound 1125).

Workup

  1. temperaturecooled
  2. stirringstirred at 0° C. for 30 minutes
  3. waitat room temperature for 2 hours
  4. extractionby extracted with ethyl acetate
  5. washwashed with 5% hydrochrolic acid and saturated brine subsequently
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99ebb29422434fd5b2c382d4cd58ec80
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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