Ammonia → HCID 15411076, compound

HRID 2187724Notes

Reaction equation

HRID 2187724 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:5]=1[C:6]([NH:8][CH:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C(=O)C)=[C:20]([CH2:28][CH2:29][CH3:30])[CH:19]=2)=[CH:14][CH:13]=1)[CH2:10]Cl)=[O:7].N>O.CN(C)C=O>[F:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:4]([F:3])[C:5]=1[C:6]1[O:7][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:28][CH2:29][CH3:30])[CH:19]=3)=[CH:14][CH:13]=2)[N:8]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 15411075HCID 15411075, compound

Product 1

HCID 15411076HCID 15411076, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

At −10° C., a solution of 3.7 g (92 mmol) of sodium hydroxide in 10 ml of water is added dropwise with stirring to a solution of 27 g (57 mmol) of 2,6-difluoro-N-[2-chloro-1-(4-(4-acetoxy-3-n-propylphenyl)phenyl)ethyl]-benzamide in 150 ml of dimethylformamide. The mixture is stirred overnight, 43 ml of a 25% strength solution of ammonia are added and the mixture is stirred overnight. The reaction mixture is then poured onto ice-water and extracted repeatedly with ethyl acetate. The combined ethyl acetate extracts are dried over MgSO4 and concentrated under reduced pressure.

Workup

  1. stirringthe mixture is stirred overnight
  2. additionThe reaction mixture is then poured onto ice-water
  3. extractionextracted repeatedly with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts are dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-638f9b7aa4bf4c06a5588cb16c469911
Source dataset
uspto-grants-2002_06
Patent number
US06410581B1

Reaction notes

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